Cyclisation of Aminyl Radicals Derived from Amino Acids
α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts el...
Saved in:
| Published in | Tetrahedron letters Vol. 38; no. 35; pp. 6301 - 6304 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
01.09.1997
Elsevier |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes. © 1997 Elsevier Science Ltd. |
|---|---|
| AbstractList | alpha-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or alpha-alkenyl chains on the amino acids with reasonable diastereoselectivity. The alpha-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes. (C) 1997 Elsevier Science Ltd. α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes. © 1997 Elsevier Science Ltd. |
| Author | Bowman, W.Russell Lewis, Kirk A Broadhurst, Michael J Coghlan, Daniel R |
| Author_xml | – sequence: 1 givenname: W.Russell surname: Bowman fullname: Bowman, W.Russell organization: Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK – sequence: 2 givenname: Michael J surname: Broadhurst fullname: Broadhurst, Michael J organization: Roche Discovery Welwyn, Broadwater Road (no 40), Welwyn Garden City, Herts. AL7 3AY, UK – sequence: 3 givenname: Daniel R surname: Coghlan fullname: Coghlan, Daniel R organization: Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK – sequence: 4 givenname: Kirk A surname: Lewis fullname: Lewis, Kirk A organization: Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK |
| BookMark | eNqNkF9LwzAUxYNMcJt-BKGPilRvmqRpnmTUvzAQdIJvoU1uILI10tTJvr1dN_aq9-U-nPO73HMmZNSEBgk5p3BNgeY3bwAcUg5MXSh5CZRTloojMqaFZCkTBR2R8cFyQiYxfkI_eQFjIsuNWfpYdT40SXDJbOWbzTJ5raw31TImd9j6NdrEtWE1iCGZGW_jKTl2vY5n-z0l7w_3i_Ipnb88PpezeWoYyC6tDAfucmkyoDXldQ61M6h4VruKFVIgy6GimCsDSljhZCHQIuZAhc0yBmxKxO6uaUOMLTr91fpV1W40Bb1Nr4f0ehtNK6mH9Fr0XLHjfrAOLhqPjcEDO6NKyY-FzHjfg2Cl74YCyvDddD169X-0d9_u3Ni3sPbY6j1hfYum0zb4P179BREMg3g |
| CitedBy_id | crossref_primary_10_1016_S0040_4039_98_02420_4 crossref_primary_10_1002_chin_199748243 crossref_primary_10_1021_ol036268n crossref_primary_10_1021_ja0201799 crossref_primary_10_1016_j_tetasy_2008_10_006 crossref_primary_10_1039_oc094003 crossref_primary_10_1016_S0957_4166_99_00525_X crossref_primary_10_1002_ejoc_202000537 crossref_primary_10_1021_ol990720e crossref_primary_10_1039_b613443m crossref_primary_10_1021_jo1002032 crossref_primary_10_1016_S1387_1609_01_01281_6 crossref_primary_10_1002_1099_0690_200008_2000_16_2927__AID_EJOC2927_3_0_CO_2_Y crossref_primary_10_1002_cssc_202101586 crossref_primary_10_1016_S0040_4020_97_10015_1 crossref_primary_10_1002_ange_202102864 crossref_primary_10_1021_acs_chemrev_1c00831 crossref_primary_10_1021_ol026366t crossref_primary_10_1002_anie_202102864 crossref_primary_10_1016_S0040_4020_00_00327_6 crossref_primary_10_1039_D1CC03853B crossref_primary_10_1016_j_tet_2008_02_107 crossref_primary_10_1021_ol990735c crossref_primary_10_1081_SCC_100104475 |
| Cites_doi | 10.1016/S0040-4039(00)91819-7 10.1021/om00011a019 10.1016/S0040-4039(00)73871-8 10.1021/jo962396w 10.1021/ja953720s 10.1016/00404-0399(50)1030L- |
| ContentType | Journal Article |
| Copyright | 1997 Elsevier Science Ltd |
| Copyright_xml | – notice: 1997 Elsevier Science Ltd |
| DBID | 1KM 1KN BLEPL DTL FCVLA AAYXX CITATION |
| DOI | 10.1016/S0040-4039(97)01413-5 |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 1997 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 | 1873-3581 |
| EndPage | 6304 |
| ExternalDocumentID | 10_1016_S0040_4039_97_01413_5 A1997XT72400053 S0040403997014135 |
| GroupedDBID | --- --K --M -ET -~X .GJ .~1 123 186 1B1 1RT 1~. 1~5 29Q 4.4 457 4G. 53G 5VS 6TJ 7-5 71M 85S 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKJ AAKOC AALRI AAOAW AAQFI AAQXK AARLI AATCM AAXUO ABFNM ABFRF ABGSF ABJNI ABMAC ABPPZ ABUDA ABYKQ ABZDS ACBEA ACDAQ ACGFS ACNCT ACNNM ACRLP ADBBV ADECG ADEZE ADMUD ADUVX AEFWE AEHWI AEKER AENEX AFFNX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGRDE AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR AZFZN BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FGOYB FIRID FLBIZ FNPLU FYGXN G-Q G8K IH2 J1W K-O KOM M2Z M41 MO0 MVM N9A O-L OAUVE OGGZJ OHT OZT P-9 P2P PC. Q38 R2- RNS ROL RPZ SCB SCC SDF SDG SDP SES SOC SPC SPCBC SSK SSP SSU SSZ T5K TN5 TWZ UQL WH7 XFK XJT XPP Y6R YK3 YR2 ZCG ZMT ~02 ~G- ~KM 1KM 1KN AAHBH AAXKI ADVLN AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED .HR 0R~ 3EH AAYOK AAYXX ABXDB ACBNA ACKIV AEBSH AFJKZ ASPBG AVWKF CITATION D0S FEDTE GBLVA HMS HVGLF HZ~ IHE O9- P-8 RIG SEW WUQ XSW YQJ ZKB ZXP |
| ID | FETCH-LOGICAL-c307t-ac404f67c201b14b60bfce942bfa3875e360a1e69c095d5f785edee6015d22303 |
| IEDL.DBID | AIKHN |
| ISICitedReferencesCount | 33 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=A1997XT72400053 |
| ISSN | 0040-4039 |
| IngestDate | Thu Sep 26 16:29:54 EDT 2024 Tue Sep 17 22:52:41 EDT 2024 Fri Nov 08 19:59:34 EST 2024 Fri Feb 23 02:33:59 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 35 |
| Keywords | HYDRAZONES AMIDYL RADICALS IMINES KINETICS RATE CONSTANTS SULFENAMIDE PRECURSORS CYCLIZATION |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c307t-ac404f67c201b14b60bfce942bfa3875e360a1e69c095d5f785edee6015d22303 |
| PageCount | 4 |
| ParticipantIDs | elsevier_sciencedirect_doi_10_1016_S0040_4039_97_01413_5 crossref_primary_10_1016_S0040_4039_97_01413_5 webofscience_primary_A1997XT72400053CitationCount webofscience_primary_A1997XT72400053 |
| PublicationCentury | 1900 |
| PublicationDate | 1997-09-01 1997-09-00 |
| PublicationDateYYYYMMDD | 1997-09-01 |
| PublicationDate_xml | – month: 09 year: 1997 text: 1997-09-01 day: 01 |
| PublicationDecade | 1990 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD |
| PublicationTitle | Tetrahedron letters |
| PublicationTitleAbbrev | TETRAHEDRON LETT |
| PublicationYear | 1997 |
| Publisher | Elsevier Ltd Elsevier |
| Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
| References | 1991, 981; Beckwith, A.L.J. Newcomb, Horner, Shahin (BIB6) 1993; 34 Jai Press, London, 1991, 83 1991, 24, 296–304; Giese, B. 1997, in print; Kappe, Th.; Kappe, C.O. in Adlington, R.M.; Baldwin, J.E.; Basak, A.; Kozyrod, R.P. Pergamon Press, Oxford, 1989; Reetz, M.T. h). Products were separated from tin residues by extraction into dil. hydrochloric acid. Products were characterised by IR Newcomb, Esker (BIB1) 1993; 28 1993, 58, 4933–4940. 1996, 118, 13–19. Duthaler, R.O. Esker, Newcomb (BIB4) 1993; 34 1994, 50, 1539; Williams, R.M. 1993, 944; Baldwin, J.E.; Fieldhouse, R.; Russell, A.T. 1995, 36, 5623–5626 and Ha, Musa, Martinez, Newcomb (BIB7) 1997; 62 Easton, C.J. in 1993, 143; Beckwith, A.L.J.; Chai, C.L.L. Aldabbagh, F.; Bowman, W.R. 1991, 30, 1531. A solution of Bu 1994, 50, 1275–1294 and 1295–1310. Esker, J.L.; Newcomb, M. 1995, 51, 7959–7980; Bowman, W.R.; Stephenson, P.T.; Young, A.R. 1996, 52, 11445–11462. Chatgilialoglu, Ballestri (BIB16) 1995; 14 eds., H. Suschitzky and G. Gribble, Elsevier Science, New York, 1996, vol. 8. 1997, 97, 53–82. Horner, J.H.; Martinez, F.N.; Musa, O.M.; Newcomb, M.; Shahin, H. SnH (1.33 equiv.) and AMBN (0.33 equiv.) in toluene were added to a solution of the precursor in refluxing toluene using a syringe pump under an atmosphere of nitrogen over 6 h (4 cm Bowman, W.R.; Stephenson, P.T.; Terrett, N.K.; Young, A.R. 1996, 48, 301–556. Bowman, W.R.; Clark, D.N.; Marmon, R.J. 1991, 32, 6441–6444 and 1992, 33, 4993–4994 1995, 117, 11124–11133; Wagner, B.D.; Ruel, G.; Lusztyk, J. 1990, 1087. C NMR, and mass spectra, and combustion analysis or accurate mass. 1994, 35, 6369–6372 and 1992, 33, 5913–5916 and 1993, 34, 5491; Barton, D.H.R.; Gero, S.D.; Quichlet-Sire, B.; Samadi, M.J. H and Maxwell, Tsanaktsidis (BIB3) 1996; 118 1994, 1–26; Porter, N.A.; Giese, B.; Curran, D.P. Smadja, W. ADLINGTON RM (WOS:A1997XT72400053.1) 1993 BOWMAN, WR (WOS:A1994PD85100049) 1994; 35 BECKWITH ALJ (WOS:A1997XT72400053.5) 1993 NEWCOMB M (WOS:A1997XT72400053.27) 1993; 28 Ha, C (WOS:A1997WX15900007) 1997; 62 BECKWITH, ALJ (WOS:A1990DV32000012) 1990 HORNER, JH (WOS:A1995TE73900012) 1995; 117 ESKER, JL (WOS:A1993MC98900018) 1993; 34 BALDWIN, JE (WOS:A1993LT95300033) 1993; 34 DUTHALER, RO (WOS:A1994MV16400001) 1994; 50 KAPPE T (WOS:A1997XT72400053.25) 1996; 8 ESKER, JL (WOS:A1993LV45300033) 1993; 58 Bowman, WR (WOS:A1996VD89200006) 1996; 52 NEWCOMB, M (WOS:A1993LV10700002) 1993; 34 Wagner, BD (WOS:A1996TQ16100002) 1996; 118 BOWMAN, WR (WOS:A1991GN23900049) 1991; 32 BOWMAN, WR (WOS:A1992JK10300040) 1992; 33 ESKER, JL (WOS:A1992JQ66000016) 1992; 33 GIESE B (WOS:A1997XT72400053.22) 1996; 48 BOWMAN, WR (WOS:A1994MT54500028) 1994; 50 CHATGILIALOGLU, C (WOS:A1995TE43400019) 1995; 14 BOWMAN, WR (WOS:A1995RN09400047) 1995; 36 WILLIAMS RM (WOS:A1997XT72400053.33) 1989 BOWMAN, WR (WOS:A1995RJ58400009) 1995; 51 BARTON, DHR (WOS:A1991FM10700002) 1991 Maxwell, BJ (WOS:A1996UK14500008) 1996; 118 Easton, CJ (WOS:A1997WG46400004) 1997; 97 REETZ, MT (WOS:A1991GY97700001) 1991; 30 BOWMAN, WR (WOS:A1994MT54500029) 1994; 50 PORTER, NA (WOS:A1991GN85000003) 1991; 24 ALDABBAGH F (WOS:A1997XT72400053.2) 1997 EASTON CJ (WOS:A1997XT72400053.17) 1991; 1 SMADJA, W (WOS:A1994MT13300001) 1994 Maxwell (10.1016/S0040-4039(97)01413-5_BIB3) 1996; 118 Esker (10.1016/S0040-4039(97)01413-5_BIB4) 1993; 34 10.1016/S0040-4039(97)01413-5_BIB5 10.1016/S0040-4039(97)01413-5_BIB10 10.1016/S0040-4039(97)01413-5_BIB11 10.1016/S0040-4039(97)01413-5_BIB2 10.1016/S0040-4039(97)01413-5_BIB12 10.1016/S0040-4039(97)01413-5_BIB9 10.1016/S0040-4039(97)01413-5_BIB13 10.1016/S0040-4039(97)01413-5_BIB8 10.1016/S0040-4039(97)01413-5_BIB14 Chatgilialoglu (10.1016/S0040-4039(97)01413-5_BIB16) 1995; 14 10.1016/S0040-4039(97)01413-5_BIB15 Newcomb (10.1016/S0040-4039(97)01413-5_BIB6) 1993; 34 Ha (10.1016/S0040-4039(97)01413-5_BIB7) 1997; 62 Newcomb (10.1016/S0040-4039(97)01413-5_BIB1) 1993; 28 |
| References_xml | – volume: 62 start-page: 2704 year: 1997 end-page: 2710 ident: BIB7 publication-title: J. Org. Chem. contributor: fullname: Newcomb – volume: 28 start-page: 1031 year: 1993 end-page: 1045 ident: BIB1 publication-title: Advances in Heterocyclic Chemistry contributor: fullname: Esker – volume: 14 start-page: 5017 year: 1995 end-page: 5018 ident: BIB16 publication-title: Organometallics contributor: fullname: Ballestri – volume: 118 start-page: 4276 year: 1996 end-page: 4283 ident: BIB3 publication-title: J. Am. Chem. Soc. contributor: fullname: Tsanaktsidis – volume: 34 start-page: 6877 year: 1993 end-page: 6880 ident: BIB4 publication-title: Tetrahedron Lett. contributor: fullname: Newcomb – volume: 34 start-page: 5523 year: 1993 end-page: 5526 ident: BIB6 publication-title: Tetrahedron Lett. contributor: fullname: Shahin – start-page: 1 year: 1994 ident: WOS:A1994MT13300001 article-title: ACYCLIC DIASTEREOFACIAL SELECTION IN INTERMOLECULAR RADICAL REACTIONS STERIC VS ELECTRONIC CONTROLS publication-title: SYNLETT contributor: fullname: SMADJA, W – volume: 62 start-page: 2704 year: 1997 ident: WOS:A1997WX15900007 article-title: Lewis acid activation and catalysis of dialkylaminyl radical reactions publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Ha, C – volume: 33 start-page: 4993 year: 1992 ident: WOS:A1992JK10300040 article-title: CYCLIZATION OF AMINYL RADICALS USING SULFENAMIDE PRECURSORS publication-title: TETRAHEDRON LETTERS contributor: fullname: BOWMAN, WR – volume: 51 start-page: 7959 year: 1995 ident: WOS:A1995RJ58400009 article-title: RADICAL CYCLIZATIONS OF IMINES AND HYDRAZONES publication-title: TETRAHEDRON contributor: fullname: BOWMAN, WR – volume: 14 start-page: 5017 year: 1995 ident: WOS:A1995TE43400019 article-title: TRIS(TRIMETHYLSILYL)GERMANE AS A RADICAL-BASED REDUCING AGENT publication-title: ORGANOMETALLICS contributor: fullname: CHATGILIALOGLU, C – volume: 117 start-page: 11124 year: 1995 ident: WOS:A1995TE73900012 article-title: KINETICS OF DIALKYLAMINIUM CATION-RADICAL REACTIONS - RADICAL CLOCKS, SOLVENT EFFECTS, ACIDITY CONSTANTS, AND RATE CONSTANTS FOR REACTIONS WITH HYDROGEN-ATOM DONORS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: HORNER, JH – start-page: 981 year: 1991 ident: WOS:A1991FM10700002 article-title: EXPEDIENT SYNTHESIS OF NATURAL (S)-SINEFUNGIN AND OF ITS C-6' EPIMER publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: BARTON, DHR – volume: 97 start-page: 53 year: 1997 ident: WOS:A1997WG46400004 article-title: Free-radical reactions in the synthesis of alpha-amino acids and derivatives publication-title: CHEMICAL REVIEWS contributor: fullname: Easton, CJ – volume: 34 start-page: 5491 year: 1993 ident: WOS:A1993LT95300033 article-title: SYNTHESIS AND ASSIGNMENT OF THE RELATIVE STEREOCHEMISTRY OF A PUTATIVE BIOSYNTHETIC PRECURSOR OF TABTOXININE BETA-LACTAM publication-title: TETRAHEDRON LETTERS contributor: fullname: BALDWIN, JE – volume: 30 start-page: 1531 year: 1991 ident: WOS:A1991GY97700001 article-title: NEW APPROACHES TO THE USE OF AMINO-ACIDS AS CHIRAL BUILDING-BLOCKS IN ORGANIC-SYNTHESIS publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: REETZ, MT – volume: 50 start-page: 1295 year: 1994 ident: WOS:A1994MT54500029 article-title: SYNTHESIS OF PYRROLIZIDINES USING AMINYL RADICALS GENERATED FROM SULFENAMIDE PRECURSORS publication-title: TETRAHEDRON contributor: fullname: BOWMAN, WR – volume: 118 start-page: 13 year: 1996 ident: WOS:A1996TQ16100002 article-title: Absolute kinetics of aminium radical reactions with olefins in acetonitrile solution publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Wagner, BD – start-page: 1087 year: 1990 ident: WOS:A1990DV32000012 article-title: DIASTEREOSELECTIVE RADICAL-ADDITION TO DERIVATIVES OF DEHYDROALANINE AND OF DEHYDROLACTIC ACID publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: BECKWITH, ALJ – volume: 28 start-page: 1031 year: 1993 ident: WOS:A1997XT72400053.27 publication-title: ADV HETEROCYCLIC CHE contributor: fullname: NEWCOMB M – volume: 34 start-page: 5523 year: 1993 ident: WOS:A1993LV10700002 article-title: RATE CONSTANTS FOR AMINYL RADICAL REACTIONS publication-title: TETRAHEDRON LETTERS contributor: fullname: NEWCOMB, M – volume: 34 start-page: 6877 year: 1993 ident: WOS:A1993MC98900018 article-title: AMIDYL RADICALS FROM N-(PHENYLTHIO)AMIDES publication-title: TETRAHEDRON LETTERS contributor: fullname: ESKER, JL – year: 1997 ident: WOS:A1997XT72400053.2 publication-title: IN PRESS CONTEMP ORG contributor: fullname: ALDABBAGH F – volume: 48 start-page: 301 year: 1996 ident: WOS:A1997XT72400053.22 publication-title: ORG REACTIONS contributor: fullname: GIESE B – volume: 58 start-page: 4933 year: 1993 ident: WOS:A1993LV45300033 article-title: CHEMISTRY OF AMIDYL RADICALS PRODUCED FROM N-HYDROXYPYRIDINE-2-THIONE IMIDATE ESTERS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ESKER, JL – year: 1989 ident: WOS:A1997XT72400053.33 publication-title: SYNTHESIS OPTICALLY contributor: fullname: WILLIAMS RM – volume: 52 start-page: 11445 year: 1996 ident: WOS:A1996VD89200006 article-title: Cascade radical cyclisations of imines publication-title: TETRAHEDRON contributor: fullname: Bowman, WR – volume: 50 start-page: 1539 year: 1994 ident: WOS:A1994MV16400001 article-title: RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS publication-title: TETRAHEDRON contributor: fullname: DUTHALER, RO – volume: 1 start-page: 83 year: 1991 ident: WOS:A1997XT72400053.17 publication-title: ADV DETAILED REACTIO contributor: fullname: EASTON CJ – volume: 50 start-page: 1275 year: 1994 ident: WOS:A1994MT54500028 article-title: GENERATION OF AMINYL RADICALS USING SULFENAMIDES AS SYNTHETIC PRECURSORS publication-title: TETRAHEDRON contributor: fullname: BOWMAN, WR – volume: 33 start-page: 5913 year: 1992 ident: WOS:A1992JQ66000016 article-title: N-ACYL-N-ALKYLCARBAMOYLOXY RADICALS - ENTRIES TO AMIDYL RADICALS BY DECARBOXYLATION AND TO ALPHA-AMIDE RADICALS BY RADICAL TRANSLOCATION publication-title: TETRAHEDRON LETTERS contributor: fullname: ESKER, JL – volume: 32 start-page: 6441 year: 1991 ident: WOS:A1991GN23900049 article-title: SULFENAMIDES AS SYNTHETIC PRECURSORS OF AMINYL RADICALS publication-title: TETRAHEDRON LETTERS contributor: fullname: BOWMAN, WR – volume: 8 year: 1996 ident: WOS:A1997XT72400053.25 publication-title: PROGR HETEROCYCLIC C contributor: fullname: KAPPE T – volume: 118 start-page: 4276 year: 1996 ident: WOS:A1996UK14500008 article-title: Cyclization of N-butyl-4-pentenylaminyl: Implications for the cyclization of alkenylaminyl radicals publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Maxwell, BJ – volume: 36 start-page: 5623 year: 1995 ident: WOS:A1995RN09400047 article-title: SYNTHESIS OF NITROGEN-HETEROCYCLES USING TANDEM RADICAL CYCLIZATION OF IMINES publication-title: TETRAHEDRON LETTERS contributor: fullname: BOWMAN, WR – volume: 24 start-page: 296 year: 1991 ident: WOS:A1991GN85000003 article-title: ACYCLIC STEREOCHEMICAL CONTROL IN FREE-RADICAL REACTIONS publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: PORTER, NA – start-page: 944 year: 1993 ident: WOS:A1997XT72400053.1 publication-title: J CHEM SOC CHEM COMM contributor: fullname: ADLINGTON RM – volume: 35 start-page: 6369 year: 1994 ident: WOS:A1994PD85100049 article-title: CYCLIZATION OF CARBINYL RADICALS ONTO IMINES AND HYDRAZONES publication-title: TETRAHEDRON LETTERS contributor: fullname: BOWMAN, WR – start-page: 143 year: 1993 ident: WOS:A1997XT72400053.5 publication-title: CHEM SOC REV contributor: fullname: BECKWITH ALJ – volume: 34 start-page: 6877 year: 1993 ident: 10.1016/S0040-4039(97)01413-5_BIB4 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)91819-7 contributor: fullname: Esker – volume: 14 start-page: 5017 year: 1995 ident: 10.1016/S0040-4039(97)01413-5_BIB16 publication-title: Organometallics doi: 10.1021/om00011a019 contributor: fullname: Chatgilialoglu – ident: 10.1016/S0040-4039(97)01413-5_BIB2 – volume: 34 start-page: 5523 year: 1993 ident: 10.1016/S0040-4039(97)01413-5_BIB6 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)73871-8 contributor: fullname: Newcomb – volume: 62 start-page: 2704 year: 1997 ident: 10.1016/S0040-4039(97)01413-5_BIB7 publication-title: J. Org. Chem. doi: 10.1021/jo962396w contributor: fullname: Ha – ident: 10.1016/S0040-4039(97)01413-5_BIB9 – ident: 10.1016/S0040-4039(97)01413-5_BIB8 – ident: 10.1016/S0040-4039(97)01413-5_BIB10 – volume: 28 start-page: 1031 year: 1993 ident: 10.1016/S0040-4039(97)01413-5_BIB1 publication-title: Advances in Heterocyclic Chemistry contributor: fullname: Newcomb – ident: 10.1016/S0040-4039(97)01413-5_BIB12 – ident: 10.1016/S0040-4039(97)01413-5_BIB11 – ident: 10.1016/S0040-4039(97)01413-5_BIB13 – ident: 10.1016/S0040-4039(97)01413-5_BIB14 – ident: 10.1016/S0040-4039(97)01413-5_BIB15 – volume: 118 start-page: 4276 year: 1996 ident: 10.1016/S0040-4039(97)01413-5_BIB3 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja953720s contributor: fullname: Maxwell – ident: 10.1016/S0040-4039(97)01413-5_BIB5 doi: 10.1016/00404-0399(50)1030L- |
| SSID | ssj0000680 |
| Score | 1.7135708 |
| Snippet | α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto... alpha-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions... |
| Source | Web of Science |
| SourceID | crossref webofscience elsevier |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 6301 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Cyclisation of Aminyl Radicals Derived from Amino Acids |
| URI | https://dx.doi.org/10.1016/S0040-4039(97)01413-5 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=A1997XT72400053 |
| Volume | 38 |
| WOS | A1997XT72400053 |
| WOSCitedRecordID | wosA1997XT72400053 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV07T8MwED71McCCeIryqDJ0gCFtXnaSMQpUBUQH1ErdosR2pEglrWhA6sJv55w4tEggEMrmxBfni33fnXx3BujJEi7U5kI3aCx0hyRc9wX6POhtGcJ3GHEcmZz8OKajqXM_I7MGhHUujAyrVLq_0umltlYtA4XmYJllMsfXwQsJ1pXBijZpQhvpyPJa0A7uHkbjLYXsGXXwnOywSeSphJSNV757XcrRyU8U9Q0zlSw03Ic9ZT5qQTXCA2iI_BB2wvrUtiNwwzWbqxAdbZFqwXOWr-faU1zux6y0G5xxb4JrMq2kvLnQApbx1TFMh7eTcKSrwxF0hsuy0GOGX59SlyGDJ6aTUCNJGaJrJWlsoxMibGrEpqA-QyOKk9T1iOBCoP9FOJoEhn0CrXyRi1PQYhNpm1ucoGZEesIlTa3EN7idotTY8zvQr_GIllUNjGgTHIYARhLASO5kSwAj0gGvRi368jMj1NO_de1to_z5Plmd151NXBnyinqjA-ZfHgtVnXOZ31-c_X9U57Bbla2VsWUX0CpeXsUlGiNF0oVm_93sqin3Ad7R1Zs |
| link.rule.ids | 315,783,787,4509,24128,27936,27937,45597,45691 |
| linkProvider | Elsevier |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV07T8MwED6VMpQF8RTl6aEDDGmTxnaSsQpUBdoOqJW6WUnsSJVKWtGA1IXfzjkPWiQQCGVzHMf5cv7uTr47AzR0CRduS2WYPFAGZaE0PIU-D3pbpvJoxCjVycmDIe-N6cOETSrgl7kwOqyy4P6c0zO2LlpaBZqtxXSqc3wpXqhgHR2saLMt2KbaPkahbr5bG3TsmmXonO6-TuPJh8garz3nJhvFYD8pqG_0UqaDunuwWxiPpJPPbx8qKjmAml-e2XYIjr-KZkWADpnHpPM8TVYz8hRkuzFLcovy9qYk0Ukl2c056URTuTyCcfdu5PeM4mgEI8JFmRpBhN8ecydC_R1aNORmGEeIbTuMAxtdEGVzM7AU9yI0oSSLHZcpqRR6X0yiQWDax1BN5ok6ARJYqLRlWzLkRVROuKB5O_RMacc4auB6dWiWeIhFXgFDrEPDEEChARR6H1sDKFgd3BI18eVXCmTp3x5tbKL8-T5dm9eZjBwd8IqsUQfrL938osq5zu5PT_8_qyuo9UaDvujfDx_PYCcvYKujzM6hmr68qgs0S9LwMhO7D71A1nQ |
| 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=Cyclisation+of+Aminyl+Radicals+Derived+from+Amino+Acids&rft.jtitle=Tetrahedron+letters&rft.au=Bowman%2C+W.Russell&rft.au=Broadhurst%2C+Michael+J&rft.au=Coghlan%2C+Daniel+R&rft.au=Lewis%2C+Kirk+A&rft.date=1997-09-01&rft.issn=0040-4039&rft.volume=38&rft.issue=35&rft.spage=6301&rft.epage=6304&rft_id=info:doi/10.1016%2FS0040-4039%2897%2901413-5&rft.externalDBID=n%2Fa&rft.externalDocID=10_1016_S0040_4039_97_01413_5 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon |