Catalytic Asymmetric Mannich-Type Reactions Using a Novel Chiral Iron Complex
Catalytic asymmetric Mannich‐type reactions using a novel chiral iron complex have been developed. The reactions proceeded smoothly in the presence of a catalyst prepared from iron(II) chloride, a BINOL derivative, and i‐Pr2NEt. The desired products were obtained in good yield with good to high enan...
Saved in:
| Published in | Advanced synthesis & catalysis Vol. 344; no. 9; pp. 929 - 931 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.10.2002
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Catalytic asymmetric Mannich‐type reactions using a novel chiral iron complex have been developed. The reactions proceeded smoothly in the presence of a catalyst prepared from iron(II) chloride, a BINOL derivative, and i‐Pr2NEt. The desired products were obtained in good yield with good to high enantioselectivity, when 3,3′‐I2BINOL was employed as a chiral ligand. A protic additive such as methanol facilitated the reactions effectively. |
|---|---|
| AbstractList | Catalytic asymmetric Mannich-type reactions using a novel chiral iron complex have been developed. The reactions proceeded smoothly in the presence of a catalyst prepared from iron(II) chloride, a BINOL derivative, and i-Pr2NEt. The desired products were obtained in good yield with good to high enantioselectivity, when 3,3'-I2BINOL was employed as a chiral ligand. A protic additive such as methanol facilitated the reactions effectively. |
| Author | Yamashita, Yasuhiro Kuriyama, Yokusu Kobayashi, Shū Ueno, Masaharu |
| Author_xml | – sequence: 1 givenname: Yasuhiro surname: Yamashita fullname: Yamashita, Yasuhiro organization: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 Japan Fax: (+81)-3-5684 0634 – sequence: 2 givenname: Masaharu surname: Ueno fullname: Ueno, Masaharu organization: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 Japan Fax: (+81)-3-5684 0634 – sequence: 3 givenname: Yokusu surname: Kuriyama fullname: Kuriyama, Yokusu organization: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 Japan Fax: (+81)-3-5684 0634 – sequence: 4 givenname: Shū surname: Kobayashi fullname: Kobayashi, Shū email: skobayas@mol.f.u-tokyo.ac.jp organization: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 Japan Fax: (+81)-3-5684 0634 |
| BookMark | eNqVkN9v0zAQxy00JLbB_5BHEEo5O3ESF4RUPNgqravYD0B7OTnelRlSp4oDLP89jlr6xAM8-XvW3Ud3nyN24FtPjE05TDiAeMULLtOcF-q5iCWHF1meT9UbJdR0OpufpLOTKx2Lt9kEJnr5WqS3j9jhfuhgnyU8YUchfAPgZVWWh2yhTW-aoXc2mYVhvaa-i3FhvHf2Pr0eNpRckrG9a31IboLzXxOTXLQ_qUn0vetMk8y71ie6XW8aenjKHq9ME-jZ7j1mNx_eX-uz9Hx5Otez89TmnKu0VlRSxW1lpSjqWuZQlHdgTa5qXgDVKyWFBctVVsv6zhTckipjS0UgVF7K7Jhdbrm2a0PoaIWbzq1NNyAHHIXheC-Ot-NWGEZhqDA6QozCcCcMMwTUSxR4G6Evt9BfVLerYB15S3swjMoUSK5iAhG7q3_v1q43o0Ld_vB9HP20G3UNDf-z-t83__MVwekW7EJPD3uw6b5jUWalxM8Xp5hdffyi1Nk7XGS_AQIYrbo |
| Cites_doi | 10.1021/cr990267k 10.1021/ja016293t 10.1021/ja017814f 10.1021/ja001642p |
| ContentType | Journal Article |
| Copyright | 2002 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
| Copyright_xml | – notice: 2002 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
| DBID | BSCLL 1KM 1KN BLEPL DTL FTWYQ AAYXX CITATION |
| DOI | 10.1002/1615-4169(200210)344:9<929::AID-ADSC929>3.0.CO;2-Z |
| DatabaseName | Istex Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2002 CrossRef |
| DatabaseTitle | Web of Science CrossRef |
| DatabaseTitleList | Web of Science |
| Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1615-4169 |
| EndPage | 931 |
| ExternalDocumentID | 10_1002_1615_4169_200210_344_9_929__AID_ADSC929_3_0_CO_2_Z 000179051900002 ADSC929 ark_67375_WNG_3SQX99HB_M |
| Genre | shortCommunication |
| GroupedDBID | -~X 05W 0R~ 1L6 1OB 1OC 23M 31~ 33P 3SF 3WU 4.4 4ZD 50Y 52U 52V 53G 5GY 5VS 66C 6P2 8-0 8-1 8UM A00 AAESR AAEVG AAHHS AAIHA AANLZ AAONW AASGY AAXRX AAZKR ABCUV ABDBF ABIJN ABJNI ABLJU ABQWH ABRJW ABXGK ACAHQ ACBWZ ACCFJ ACCZN ACGFS ACGOF ACMXC ACNCT ACPOU ACXBN ACXQS ADBBV ADBTR ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFZJQ AHBTC AI. AIACR AITYG AIURR AIWBW AJBDE ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ASPBG ATUGU AVWKF AZFZN AZVAB BDRZF BFHJK BHBCM BMXJE BNHUX BOGZA BRXPI BSCLL CS3 DCZOG DPXWK DR2 DRFUL DRMAN DRSTM EBS EJD F5P FEDTE FUBAC G-S GNP GODZA HBH HF~ HGLYW HHY HHZ HVGLF HZ~ IX1 JPC KBYEO KQQ LATKE LAW LEEKS LITHE LOXES LUTES LYRES M21 MEWTI MRFUL MRMAN MRSTM MSFUL MSMAN MSSTM MXFUL MXMAN MXSTM MY~ NNB O66 O9- OIG P2P P2W P4E QRW R.K RJQFR ROL RWI RX1 RYL SUPJJ TUS V2E VH1 W99 WBKPD WH7 WIH WIJ WIK WJL WOHZO WXSBR WYJ XPP XV2 ~S- 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED AAYXX CITATION |
| ID | FETCH-LOGICAL-c4119-b9e7e81c8c526bb54067d0ca49b160ebf952c0c193b5bda61ce9767d8e0294753 |
| IEDL.DBID | DR2 |
| ISICitedReferencesCount | 30 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000179051900002 |
| ISSN | 1615-4150 |
| IngestDate | Fri Aug 23 03:09:17 EDT 2024 Wed Sep 18 04:56:01 EDT 2024 Fri Nov 08 20:07:02 EST 2024 Sat Aug 24 00:46:25 EDT 2024 Wed Oct 30 09:49:18 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 9 |
| Keywords | Lewis acid AQUA COMPLEXES DIELS-ALDER REACTIONS LIGANDS Mannich reaction iron asymmetric catalysis WATER |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c4119-b9e7e81c8c526bb54067d0ca49b160ebf952c0c193b5bda61ce9767d8e0294753 |
| Notes | ArticleID:ADSC929 istex:832877610C85C0EF95DE122B2EDE187943585250 ark:/67375/WNG-3SQX99HB-M |
| PageCount | 3 |
| ParticipantIDs | crossref_primary_10_1002_1615_4169_200210_344_9_929__AID_ADSC929_3_0_CO_2_Z webofscience_primary_000179051900002 wiley_primary_10_1002_1615_4169_200210_344_9_929_AID_ADSC929_3_0_CO_2_Z_ADSC929 webofscience_primary_000179051900002CitationCount istex_primary_ark_67375_WNG_3SQX99HB_M |
| PublicationCentury | 2000 |
| PublicationDate | October 2002 |
| PublicationDateYYYYMMDD | 2002-10-01 |
| PublicationDate_xml | – month: 10 year: 2002 text: October 2002 |
| PublicationDecade | 2000 |
| PublicationPlace | Weinheim |
| PublicationPlace_xml | – name: Weinheim – name: WEINHEIM |
| PublicationTitle | Advanced synthesis & catalysis |
| PublicationTitleAbbrev | ADV SYNTH CATAL |
| PublicationTitleAlternate | Adv. Synth. Catal |
| PublicationYear | 2002 |
| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley |
| Publisher_xml | – name: WILEY-VCH Verlag – name: WILEY‐VCH Verlag – name: Wiley |
| References | E. P. Kündig , C. M. Saudan , F. Viton , Adv. Synth. Catal. 2001, 343, 51 S. Kobayashi , M. Ueno , H. Ishitani , J. Am. Chem. Soc. 1998, 120, 431 H. Ishitani , T. Kitazawa , S. Kobayashi , Tetrahedron Lett. 1999, 40, 2161 Y. Yamashita , H. Ishitani , H. Shimizu , S. Kobayashi , J. Am. Chem. Soc. 2002, 124, 3292. H.-J. Knölker , A. Braier , D. J. Brocher , S. Cammerer , W. Frohner , P. Gonser , H. Hermann , D. Herzberg , K. R. Reddy , G. Rohde , Pure Appl. Chem. 2001, 73, 1075 H. Ishitani , M. Ueno , S. Kobayashi , J. Am. Chem. Soc. 2000, 122, 8180 Whiting et al. have reported catalytic asymmetric aza-DielsAlder reactions using a chiral iron-bisoxazoline complex, see: S. Bromidge , P. C. Wilson , A. Whiting , Tetrahedron Lett. 1998, 39, 8905. In some metal-catalyzed asymmetric reactions, water affected the yields and selectivities, see: S. Ribe , P. Wipf , Chem. Commun. 2001, 299. H. Ishitani , S. Komiyama , Y. Hasegawa , S. Kobayashi , J. Am. Chem. Soc. 2000, 122, 762 N. Khiar , I. Fernández , F. Alcudia , Tetrahedron Lett. 1993, 34, 123. T. Kauffmann , Angew. Chem. Int. Ed. Engl. 1996, 35, 386 T. Gastner , H. Ishitani , R. Akiyama , S. Kobayashi , Angew. Chem. Int. Ed. Engl. 2001, 40, 1896. H.-J. Knölker , Chem. Rev. 2000, 100, 2941 H. Ishitani , M. Ueno , S. Kobayashi , J. Am. Chem. Soc. 1997, 119, 7153 S. Kanemasa , Y. Oderaotoshi , H. Yamamoto , J. Tanaka , E. Wada , D. P. Curran , J. Org. Chem. 1997, 62, 6454 S. Kobayashi , Y. Hasegawa , H. Ishitani , Chem. Lett. 1998, 1131 M. E. Bruin , E. P. Kündig , Chem. Commun. 1998, 2635 K. Ruck-Braun , M. Mikulas , P. Amrhein , Synthesis 1999, 727 D. Astruc , Chem. Met.-Carbon Bond 1987, 4, 625. J. P. Collman , Z. Wang , Chemtracts 1999, 12, 229 S. Kobayashi , K. Kusakabe , S. Komiyama , H. Ishitani , J. Org. Chem. 1999, 64, 4220 B. Meunier , Chem. Rev. 1992, 92, 1411 S. Kobayashi , S. Komiyama , H. Ishitani , Angew. Chem. Int. Ed. Engl. 1998, 37, 979 M. Redlich , S. J. Mahmood , M. F. Mayer , M. M. Hossain , Synth. Commun. 2000, 30, 1401 M. F. Mayer , M. M. Hossain , J. Org. Chem. 1998, 63, 6839 H. Ishitani , S. Komiyama , S. Kobayashi , Angew. Chem. Int. Ed. Engl. 1998, 37, 3186 Wulff et al. also reported catalytic asymmetric Mannich-type reactions of imines prepared from o-aminophenol using a chiral Zr-VAPOL complex, see: S. Xue , S. Yu , Y. Deng , W. D. Wulff , Angew. Chem. Int. Ed. Engl. 2001, 40, 2271. E. P. Kündig , B. Bourdin , G. Bernardinelli , Angew. Chem. Int. Ed. Engl. 1994, 33, 1856 S. Kanemasa , Y. Oderaotoshi , S. Sakaguchi , H. Yamamoto , J. Tanaka , E. Wada , J. Am. Chem. Soc. 1998, 120, 3074. S. Kobayashi , K. Kusakabe , H. Ishitani , Org. Lett. 2000, 2, 1225 E. J. Corey , N. Imai , H.-Y. Zhang , J. Am. Chem. Soc. 1991, 113, 728. S. G. Davies , Aldrichimica Acta 1990, 23, 31. W. A. Donaldson , Current Organic Chemistry 2000, 4, 837 M. F. Mayer , Q. Wang , M. M. Hossain , J. Organometallic Chem. 2001, 630, 78. H. Ishitani , Y. Yamashita , H. Shimizu , S. Kobayashi , J. Am. Chem. Soc. 2000, 122, 5403 2001; 343 1997; 62 1991; 113 1997; 119 2000; 4 1987; 4 1998 1999; 64 2000; 2 1999; 40 1998; 63 1996; 35 2001; 40 1999 1998; 37 2001; 630 1992; 92 1993; 34 1998; 39 1990; 23 2001 2002; 124 2000; 30 1999; 12 1994; 33 2000; 100 2000; 122 2001; 73 1998; 120 Kobayashi, S (WOS:000071624500028) 1998; 120 Kundig, EP (WOS:000168192500010) 2001; 343 Kobayashi, S (WOS:000086795200013) 2000; 2 Kanemasa, S (WOS:000073072700011) 1998; 120 Knolker, HJ (WOS:000172026900005) 2001; 73 Ishitani, H (WOS:000087540500027) 2000; 122 KHIAR, N (WOS:A1993KE37100028) 1993; 34 Ishitani, H (WOS:000077478100032) 1998; 37 Redlich, M (WOS:000086376200007) 2000; 30 KUNDIG, EP (WOS:A1994PL60100017) 1994; 33 Ishitani, H (WOS:000089301600009) 2000; 122 Knolker, HJ (WOS:000088838500009) 2000; 100 MEUNIER, B (WOS:A1992JR60600008) 1992; 92 ASTRUC D (WOS:000179051900002.1) 1987; 4 Mayer, MF (WOS:000170934300010) 2001; 630 Viton, F (WOS:000175369100018) 2002; 124 COREY, EJ (WOS:A1991ET68200081) 1991; 113 Kobayashi, S (WOS:000073339000030) 1998; 37 Gastner, T (WOS:000168891800016) 2001; 40 Ishitani, H (WOS:A1997XN52500028) 1997; 119 COLLMAN JP (WOS:000179051900002.4) 1999; 12 Kanemasa, S (WOS:A1997XX49000004) 1997; 62 Ishitani, H (WOS:000078887300038) 1999; 40 Kauffmann, T (WOS:A1996UB21300002) 1996; 35 Ribe, S (WOS:000166923600001) 2001 Xue, S (WOS:000169457300010) 2001; 40 Bromidge, S (WOS:000076995300042) 1998; 39 Ruck-Braun, K (WOS:000080264900001) 1999 Yamashita, Y (WOS:000174793400027) 2002; 124 Bruin, ME (WOS:000077430700042) 1998 Kobayashi, S (WOS:000077326500030) 1998 DAVIES SG (WOS:000179051900002.6) 1990; 23 Ishitani, H (WOS:000085294700002) 2000; 122 Kobayashi, S (WOS:000080849000002) 1999; 64 Mayer, MF (WOS:000076380300021) 1998; 63 Donaldson, WA (WOS:000088981700004) 2000; 4 |
| References_xml | – volume: 92 start-page: 1411 year: 1992 publication-title: Chem. Rev. – volume: 40 start-page: 2161 year: 1999 publication-title: Tetrahedron Lett. – volume: 113 start-page: 728 year: 1991 publication-title: J. Am. Chem. Soc. – volume: 40 start-page: 1896 year: 2001 publication-title: Angew. Chem. Int. Ed. Engl. – volume: 122 start-page: 8180 year: 2000 publication-title: J. Am. Chem. Soc. – volume: 124 start-page: 3292 year: 2002 publication-title: J. Am. Chem. Soc. – start-page: 2635 year: 1998 publication-title: Chem. Commun. – volume: 39 start-page: 8905 year: 1998 publication-title: Tetrahedron Lett. – volume: 119 start-page: 7153 year: 1997 publication-title: J. Am. Chem. Soc. – volume: 64 start-page: 4220 year: 1999 publication-title: J. Org. Chem. – volume: 122 start-page: 762 year: 2000 publication-title: J. Am. Chem. Soc. – volume: 122 start-page: 5403 year: 2000 publication-title: J. Am. Chem. Soc. – volume: 23 start-page: 31 year: 1990 publication-title: Aldrichimica Acta – volume: 630 start-page: 78 year: 2001 publication-title: J. Organometallic Chem. – volume: 37 start-page: 979 year: 1998 publication-title: Angew. Chem. Int. Ed. Engl. – start-page: 727 year: 1999 publication-title: Synthesis – volume: 73 start-page: 1075 year: 2001 publication-title: Pure Appl. Chem. – volume: 34 start-page: 123 year: 1993 publication-title: Tetrahedron Lett. – volume: 100 start-page: 2941 year: 2000 publication-title: Chem. Rev. – volume: 4 start-page: 625 year: 1987 publication-title: Chem. Met.‐Carbon Bond – volume: 12 start-page: 229 year: 1999 publication-title: Chemtracts – volume: 30 start-page: 1401 year: 2000 publication-title: Synth. Commun. – volume: 2 start-page: 1225 year: 2000 publication-title: Org. Lett. – volume: 63 start-page: 6839 year: 1998 publication-title: J. Org. Chem. – volume: 40 start-page: 2271 year: 2001 publication-title: Angew. Chem. Int. Ed. Engl. – volume: 4 start-page: 837 year: 2000 publication-title: Current Organic Chemistry – volume: 120 start-page: 3074 year: 1998 publication-title: J. Am. Chem. Soc. – volume: 33 start-page: 1856 year: 1994 publication-title: Angew. Chem. Int. Ed. Engl. – volume: 343 start-page: 51 year: 2001 publication-title: Adv. Synth. Catal. – volume: 37 start-page: 3186 year: 1998 publication-title: Angew. Chem. Int. Ed. Engl. – start-page: 299 year: 2001 publication-title: Chem. Commun. – start-page: 1131 year: 1998 publication-title: Chem. Lett. – volume: 35 start-page: 386 year: 1996 publication-title: Angew. Chem. Int. Ed. Engl. – volume: 62 start-page: 6454 year: 1997 publication-title: J. Org. Chem. – volume: 120 start-page: 431 year: 1998 publication-title: J. Am. Chem. Soc. – volume: 37 start-page: 979 year: 1998 ident: WOS:000073339000030 article-title: The first enantioselective aza-Diels-Alder reactions of imino dienophiles on use of a chiral zirconium catalyst publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kobayashi, S – volume: 30 start-page: 1401 year: 2000 ident: WOS:000086376200007 article-title: Silica supported catalysis: A practical use of an iron Lewis acid publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: Redlich, M – volume: 119 start-page: 7153 year: 1997 ident: WOS:A1997XN52500028 article-title: Catalytic enantioselective mannich-type reactions using a novel chiral zirconium catalyst publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ishitani, H – volume: 120 start-page: 3074 year: 1998 ident: WOS:000073072700011 article-title: Transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2 '-bis(4-phenyloxazoline). Effective catalysis in Diels-Alder reactions showing excellent enantioselectivity, extreme chiral amplification, and high tolerance to water, alcohols, amines, and acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kanemasa, S – start-page: 727 year: 1999 ident: WOS:000080264900001 article-title: Organoiron compounds for selective organic transformations publication-title: SYNTHESIS-STUTTGART contributor: fullname: Ruck-Braun, K – volume: 120 start-page: 431 year: 1998 ident: WOS:000071624500028 article-title: Catalytic asymmetric synthesis of both syn- and anti-beta-amino alcohols publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kobayashi, S – volume: 100 start-page: 2941 year: 2000 ident: WOS:000088838500009 article-title: Efficient synthesis of tricarbonyliron-diene complexes - Development of an asymmetric catalytic complexation publication-title: CHEMICAL REVIEWS doi: 10.1021/cr990267k contributor: fullname: Knolker, HJ – volume: 92 start-page: 1411 year: 1992 ident: WOS:A1992JR60600008 article-title: METALLOPORPHYRINS AS VERSATILE CATALYSTS FOR OXIDATION REACTIONS AND OXIDATIVE DNA CLEAVAGE publication-title: CHEMICAL REVIEWS contributor: fullname: MEUNIER, B – volume: 343 start-page: 51 year: 2001 ident: WOS:000168192500010 article-title: Chiral cyclopentadienyl-iron and -ruthenium Lewis acids containing the electron-poor BIPHOP-F ligand: a comparison as catalysts in an asymmetric Diels-Alder reaction publication-title: ADVANCED SYNTHESIS & CATALYSIS contributor: fullname: Kundig, EP – volume: 124 start-page: 3292 year: 2002 ident: WOS:000174793400027 article-title: Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja016293t contributor: fullname: Yamashita, Y – volume: 62 start-page: 6454 year: 1997 ident: WOS:A1997XX49000004 article-title: Cationic aqua complexes of the C-2-symmetric trans-chelating ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline). Absolute chiral induction in Diels-Alder reactions catalyzed by water-tolerant enantiopure Lewis acids publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kanemasa, S – volume: 113 start-page: 728 year: 1991 ident: WOS:A1991ET68200081 article-title: DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: COREY, EJ – volume: 2 start-page: 1225 year: 2000 ident: WOS:000086795200013 article-title: Chiral catalyst optimization using both solid-phase and liquid-phase methods in asymmetric aza Diels-Alder reactions publication-title: ORGANIC LETTERS contributor: fullname: Kobayashi, S – volume: 4 start-page: 625 year: 1987 ident: WOS:000179051900002.1 publication-title: CHEM METAL CARBON BO contributor: fullname: ASTRUC D – volume: 40 start-page: 2161 year: 1999 ident: WOS:000078887300038 article-title: Efficient catalytic enantioselective Mannich-type reactions using a zirconium-bis(binaphthol)methane complex publication-title: TETRAHEDRON LETTERS contributor: fullname: Ishitani, H – volume: 33 start-page: 1856 year: 1994 ident: WOS:A1994PL60100017 article-title: ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY A CHIRAL IRON LEWIS-ACID publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: KUNDIG, EP – volume: 40 start-page: 2271 year: 2001 ident: WOS:000169457300010 article-title: Active site design in a chemzyme: Development of a highly asymmetric and remarkably temperature-independent catalyst for the imino aldol reaction publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Xue, S – volume: 630 start-page: 78 year: 2001 ident: WOS:000170934300010 article-title: An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: Mayer, MF – volume: 23 start-page: 31 year: 1990 ident: WOS:000179051900002.6 publication-title: ALDRICHIM ACTA contributor: fullname: DAVIES SG – volume: 124 start-page: 4968 year: 2002 ident: WOS:000175369100018 article-title: Iron and ruthenium Lewis acid catalyzed asymmetric 1,3-dipolar cycloaddition reactions between nitrones and enals publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja017814f contributor: fullname: Viton, F – volume: 12 start-page: 229 year: 1999 ident: WOS:000179051900002.4 publication-title: CHEMTRACTS contributor: fullname: COLLMAN JP – volume: 63 start-page: 6839 year: 1998 ident: WOS:000076380300021 article-title: Catalytic preparation of aziridines with an iron Lewis acid publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Mayer, MF – volume: 122 start-page: 762 year: 2000 ident: WOS:000085294700002 article-title: Catalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure alpha-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines, and hydrogen cyanide using a chiral zirconium catalyst publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ishitani, H – volume: 73 start-page: 1075 year: 2001 ident: WOS:000172026900005 article-title: Recent applications of tricarbonyliron-diene complexes to organic synthesis publication-title: PURE AND APPLIED CHEMISTRY contributor: fullname: Knolker, HJ – volume: 64 start-page: 4220 year: 1999 ident: WOS:000080849000002 article-title: A switch of enantiofacial selectivities using designed similar chiral ligands in zirconium-catalyzed asymmetric aza Diels-Alder reactions publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kobayashi, S – volume: 34 start-page: 123 year: 1993 ident: WOS:A1993KE37100028 article-title: C2-SYMMETRICAL BIS-SULFOXIDES AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC DIELS-ALDER REACTIONS publication-title: TETRAHEDRON LETTERS contributor: fullname: KHIAR, N – volume: 39 start-page: 8905 year: 1998 ident: WOS:000076995300042 article-title: A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza-Diels-Alder reaction of an imino dienophile. publication-title: TETRAHEDRON LETTERS contributor: fullname: Bromidge, S – start-page: 1131 year: 1998 ident: WOS:000077326500030 article-title: Chiral zirconium-catalyzed asymmetric mannich-type reactions using acylhydrazones as imine equivalents publication-title: CHEMISTRY LETTERS contributor: fullname: Kobayashi, S – volume: 122 start-page: 5403 year: 2000 ident: WOS:000087540500027 article-title: Highly anti-selective catalytic asymmetric aldol reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ishitani, H – volume: 37 start-page: 3186 year: 1998 ident: WOS:000077478100032 article-title: Catalytic, enantioselective synthesis of alpha-aminonitriles with a novel zirconium catalyst publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Ishitani, H – volume: 122 start-page: 8180 year: 2000 ident: WOS:000089301600009 article-title: Enantioselective mannich-type reactions using a novel chiral zirconium catalyst for the synthesis of optically active beta-amino acid derivatives publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja001642p contributor: fullname: Ishitani, H – volume: 40 start-page: 1896 year: 2001 ident: WOS:000168891800016 article-title: Highly enantioselective allylation of imines with a chiral zirconium catalyst publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Gastner, T – volume: 4 start-page: 837 year: 2000 ident: WOS:000088981700004 article-title: Stoichiometric applications of acyclic pi-organoiron complexes to organic synthesis publication-title: CURRENT ORGANIC CHEMISTRY contributor: fullname: Donaldson, WA – volume: 35 start-page: 386 year: 1996 ident: WOS:A1996UB21300002 article-title: Nonstabilized alkyl complexes and alkyl-cyano-ate complexes of iron(II) and cobalt(II) as new reagents in organic synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kauffmann, T – start-page: 299 year: 2001 ident: WOS:000166923600001 article-title: Water-accelerated organic transformations publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Ribe, S – start-page: 2635 year: 1998 ident: WOS:000077430700042 article-title: A new chiral ligand for the Fe-Lewis acid catalysed asymmetric Diels-Alder reaction publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Bruin, ME |
| SSID | ssj0017877 |
| Score | 1.868189 |
| Snippet | Catalytic asymmetric Mannich‐type reactions using a novel chiral iron complex have been developed. The reactions proceeded smoothly in the presence of a... Catalytic asymmetric Mannich-type reactions using a novel chiral iron complex have been developed. The reactions proceeded smoothly in the presence of a... |
| Source | Web of Science |
| SourceID | crossref webofscience wiley istex |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 929 |
| SubjectTerms | asymmetric catalysis Chemistry Chemistry, Applied Chemistry, Organic iron Lewis acid Mannich reaction Physical Sciences Science & Technology |
| Title | Catalytic Asymmetric Mannich-Type Reactions Using a Novel Chiral Iron Complex |
| URI | https://api.istex.fr/ark:/67375/WNG-3SQX99HB-M/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2F1615-4169%28200210%29344%3A9%3C929%3A%3AAID-ADSC929%3E3.0.CO%3B2-Z http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000179051900002 |
| Volume | 344 |
| WOS | 000179051900002 |
| WOSCitedRecordID | wos000179051900002 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwvV1Nb9QwELWqIgEXyqcIBeRDi-CQbWInTrwgpG22ZQvqrmipWPVixY6jVm130W6KWk78BC78QX4JYzsJbcUBJISUQ5RYM8rz2H6Oxm8QWmEqoWkeFD5PysSPylT7vCTKN1JpsMPIi9gm0WwP2WAvejuOxwuoas7COH2I9oebGRl2vjYDPJfztV-ioYaq-EAnODAxm2kQwN6ZRhH0LF-lGSz7cAdXb6vv9_q77sEG7QSdbLRK14m_DxN3SBOTB9bfaTWnQohgW5HFmY-D66hbO11rXT53Dl-Auy5_BZa73QtuXjsnL8HFpdXumum4sysr3GVSbFe1zSX0vcHDJbMcdU4r2VFfrkhF_m_AbqNbNU3GPRfXd9CCntxFN7KmOt09NMrMf6dzeI178_OTE1MYTGFT8vlQHfz4-s3sr_GOdsc25thmRuAcD6ef9THODg5nYH1rNp1gMyEe67P7aG9z40M28OviEL6KwpD7kutEp6FKVUyYlEA8WVIEKo-4DFmgZcljogIF_FTGsshZqDQwr6RIdUB4BJu0B2hxMp3ohwiTXOWUcV1SpiNK4pyWrExlmUK4EhoxD71rOlF8chogwqk9E2FAFQZU4SAVAKjgArATAoAUNZCCikBkI0HEvoee2ThoTeWzI5Ndl8Ti4_CNoLvvx5wP1sW2h1YuBkrb3mocGVk1U-81IB4K_6RZVku-G6mDykMjGyl_8zm__5rm0aN_bnEZ3XSVd0zi5GO0WM1O9RMggJV8agfsT_aeOE4 |
| link.rule.ids | 315,783,787,1378,27936,27937,46306,46730 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwvV1Lb9QwEB6VVqJcylukvHJoERy8Tey8vCCkbbZll3Z3RR9i1YuVOI5atd1F213UcuIncOIH8ksYx0loKw4gIaQcoiSakT-P7c_W5BuAlUCGLEqcjPAwD4mXR4rwnEqipdJwh5FkfpFE0-sHnX3v_dAfzsGs-hfG6EPUB256ZBTztR7g-kB67ZdqqOYqBPkERypWpBo4uHlmnoddy1dZjOs-3uHV6rZJq71rHmywhtOIB6tsnZKDG7CA8wTTFR_aO7XqlIsxXNRkMfZ95yY0S69rtc-XxuMr9Nfkb9B0s3nJz1vj5TX6uLLeLeiuO7-2xl2lxcW6tnkbvleImHSW48Zsmjbkl2tikf8dsjuwVDJlu2VC-y7MqdE9WIyrAnX3YRDro6cLfG23zi5OT3VtMGnrqs9H8vDH1296i23vKPPnxpldJEfYid0ff1Yndnx4NEHr3cl4ZOs58USdP4D9zY29uEPK-hBEeq7LScpVqCJXRtKnQZoi9wzCzJGJx1M3cFSac59KRyJFTf00SwJXKiRfYRYph3IP92kPYX40HqlHYNNEJizgKmeB8hj1E5YHeZTmEUYsZV5gwVbVi-KTkQERRvCZCg2q0KAKA6lAQAUXiJ0QCKQogRRMOCIeCCoOLHhRBEJtKpkc6wS70Bcf--8E2_0w5LyzLnoWrFyOlPr7QuZIK6vpkq8OtcD9k8_iUvVdqx1MLRgUofI3zfl9a6pHy__c4nNY7Oz1tsV2t7_1GG6ZQjw6j_IJzE8nM_UU-eA0fVaM3p-cqTxm |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwvV1Nb9QwEB2VVipc-EaEzxxaBIdsEztx4gUhbbNddindhZaKVS9W4jhq1Xa32qao5cRP4MIf5JcwjpPQVhxAQkg5RIk1ozyP7Wdr8gZgicmQRombOTzMQ8fPI-XwnEhHS6XhDiPJgjKJZmPI-tv-23EwnoOi_hfG6EM0B256ZJTztR7gR1m-8ks0VFMVB-kERyZWZhq4uHemvo89y5dpjMs-3uHVGXSdTnfLPFijLbcVj5bpKnF2rsCCz5Ayayq12YhOeRjCZUkWYz9wF6FdeV1pfD43Hl-gvzZ_habb7XN-XhsvL9HHheVuQffc6aUl7iIrLpe13g34XgNisln2WydF2pJfLmlF_m_EbsL1iifbHRPYt2BOTW7D1bguT3cHRrE-eDrD13bn-OzwUFcGk7au-bwnd398_aY32PamMv9tHNtlaoSd2MPpZ3Vgx7t7M7Q-mE0ntp4RD9TpXdjurX2M-05VHcKRvudxJ-UqVJEnIxkQlqbIPFmYuTLxeeoxV6U5D4h0JRLUNEizhHlSIfUKs0i5hPu4S7sH85PpRN0HmyQyoYyrnDLlUxIkNGd5lOYRxiuhPrNgve5EcWREQISReyZCgyo0qMJAKhBQwQViJwQCKSogBRWuiEeCiB0LnpVx0JhKZvs6vS4MxKfhG0G3Pow576-KDQuWzgdK074UOdK6arrgq0ss8P6kWVxpvmutg8KCURkpf_M5v_-a-tGDf27xKSy-7_bEu8Fw_SFcM1V4dBLlI5gvZifqMZLBIn1Sjt2ffN87FQ |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Catalytic+Asymmetric+Mannich-Type+Reactions+Using+a+Novel+Chiral+Iron+Complex&rft.jtitle=Advanced+synthesis+%26+catalysis&rft.au=Yamashita%2C+Yasuhiro&rft.au=Ueno%2C+Masaharu&rft.au=Kuriyama%2C+Yokusu&rft.au=Kobayashi%2C+Sh%C5%AB&rft.date=2002-10-01&rft.pub=WILEY-VCH+Verlag&rft.issn=1615-4150&rft.eissn=1615-4169&rft.volume=344&rft.issue=9&rft.spage=929&rft.epage=931&rft_id=info:doi/10.1002%2F1615-4169%28200210%29344%3A9%3C929%3A%3AAID-ADSC929%3E3.0.CO%3B2-Z&rft.externalDBID=n%2Fa&rft.externalDocID=ark_67375_WNG_3SQX99HB_M |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1615-4150&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1615-4150&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1615-4150&client=summon |