New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction
New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8), (9), (14) and (15) were obtained through simple steps starting from chiral 4-ethenylpyrrolidin-2-ones (2) and (3). On the other hand, starting from pyrrolidine (16), an epimerisation reaction occurred, which was explained through forma...
Saved in:
| Published in | Heterocycles Vol. 51; no. 10; pp. 2463 - 2470 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier
01.10.1999
|
| Subjects | |
| Online Access | Get more information |
Cover
Loading…
| Abstract | New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8), (9), (14) and (15) were obtained through simple steps starting from chiral 4-ethenylpyrrolidin-2-ones (2) and (3). On the other hand, starting from pyrrolidine (16), an epimerisation reaction occurred, which was explained through formation of the bicyclic ammonium salt (18). Nucleophilic addition of Et2Zn to benzaldehyde, carried out in the presence of 8, gave (S)-1-phenyl-1-propanol in 28% e.e. |
|---|---|
| AbstractList | New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8), (9), (14) and (15) were obtained through simple steps starting from chiral 4-ethenylpyrrolidin-2-ones (2) and (3). On the other hand, starting from pyrrolidine (16), an epimerisation reaction occurred, which was explained through formation of the bicyclic ammonium salt (18). Nucleophilic addition of Et2Zn to benzaldehyde, carried out in the presence of 8, gave (S)-1-phenyl-1-propanol in 28% e.e. |
| Author | Galeazzi, R Orena, M Fava, C Mobbili, G |
| Author_xml | – sequence: 1 givenname: C surname: Fava fullname: Fava, C – sequence: 2 givenname: R orcidid: 0000-0003-1792-654X surname: Galeazzi fullname: Galeazzi, R – sequence: 3 givenname: G surname: Mobbili fullname: Mobbili, G – sequence: 4 givenname: M surname: Orena fullname: Orena, M |
| BookMark | eNqNj09LwzAYh3OY4DY9-QV6l2jS5G0Tb6P4D4aC7D7S5C2NtElJO-a-vav6ATz9nsPDD54VWYQYkJAbzu6EVuW9jT3VmqpCqgVZMqGAguTykqzG8ZMxpphSS_LxhsfMtj6ZLhM0mKGd2lNneh9ijzMOp5Ri550POD5km5AdAn4NaCd0GQ6-x-RHM_kYsoTGznBFLhrTjXj9t2uye3rcVS90-_78Wm22NPBSTRRcwVA7Y1QhQDhe5pIXBsE5WaKWdQ1QNraxYGvrwJaqAM2hFtDUwkmVr8nt7-0R69iM1mOwuB-S70067dlcKHIQ8gxcn231f7vy009SFQ9hyr8BuBlntw |
| ContentType | Journal Article |
| DBID | 1KM BLEPL DTL FGRAT |
| DOI | 10.3987/com-99-8648 |
| DatabaseName | Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 1999 |
| DatabaseTitle | Web of Science |
| DatabaseTitleList | Web of Science |
| Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Chemistry |
| EndPage | 2470 |
| ExternalDocumentID | 000083253400019 |
| GroupedDBID | -~X 1B1 1KM 3L6 53G 5GY ABTAH AENEX AHWXS AI. ALMA_UNASSIGNED_HOLDINGS B.R BLEPL CS3 DTL DU5 EBS EJD F5P GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED IHE P2P RIG SJN TN5 UPT VH1 XPP Y6R ZE2 ZY4 |
| ID | FETCH-LOGICAL-n178t-5d60e9daa86353d172416ae5dd47e94bb557fcfc5cbcd5c7865915b35fb3d482 |
| ISICitedReferencesCount | 5 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000083253400019 |
| ISSN | 0385-5414 |
| IngestDate | Fri Oct 18 20:08:36 EDT 2024 Thu Apr 20 20:40:07 EDT 2023 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 10 |
| Keywords | ASYMMETRIC ALDOL REACTION ACID ACYLATION SILYL ENOL ETHERS MN(III) ALDEHYDES NICOTINIC ACETYLCHOLINE-RECEPTORS CONVENIENT APPROACH DIAMINE CYCLIZATION |
| Language | English |
| LinkModel | OpenURL |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-n178t-5d60e9daa86353d172416ae5dd47e94bb557fcfc5cbcd5c7865915b35fb3d482 |
| ORCID | 0000-0003-1792-654X |
| PageCount | 8 |
| ParticipantIDs | webofscience_primary_000083253400019 webofscience_primary_000083253400019CitationCount |
| PublicationCentury | 1900 |
| PublicationDate | 1999-10-01 |
| PublicationDateYYYYMMDD | 1999-10-01 |
| PublicationDate_xml | – month: 10 year: 1999 text: 1999-10-01 day: 01 |
| PublicationDecade | 1990 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD |
| PublicationTitle | Heterocycles |
| PublicationTitleAbbrev | HETEROCYCLES |
| PublicationYear | 1999 |
| Publisher | Elsevier |
| Publisher_xml | – name: Elsevier |
| References | Holladay, MW (WOS:000072030400001) 1998; 41 Oriyama, T (WOS:A1996VU40500024) 1996; 37 Galeazzi, R (WOS:A1996TL97400032) 1996; 52 KOBAYASHI, S (WOS:A1989T380700034) 1989 Oriyama, T (WOS:000071241100016) 1998; 39 Galeazzi, R (WOS:A1997WD63200021) 1997; 8 YANG, BV (WOS:A1993KR07900007) 1993 KOBAYASHI, S (WOS:A1991FN00500030) 1991; 113 Oriyama, T (WOS:000073490400047) 1998; 39 Abreo, MA (WOS:A1996TW13600003) 1996; 39 Asami, M (WOS:A1997XQ00100027) 1997; 70 Sano, T (WOS:000079524500038) 1999 KOBAYASHI, S (WOS:A1995TD21600019) 1995; 6 KOBAYASHI, S (WOS:A1994PN45200078) 1994; 116 Mukaiyama, T (WOS:A1996WD20700001) 1996; 29 CARDILLO, B (WOS:A1995TG34000025) 1995 |
| References_xml | – start-page: 195 year: 1993 ident: WOS:A1993KR07900007 article-title: MILD AND SELECTIVE DEBENZYLATION OF TERTIARY-AMINES USING ALPHA-CHLOROETHYL CHLOROFORMATE publication-title: SYNLETT contributor: fullname: YANG, BV – start-page: 1159 year: 1995 ident: WOS:A1995TG34000025 article-title: CYCLIZATION OF A CHIRAL N-CROTYL METHOXYCARBONYLACETAMIDE MEDIATED BY MN(III) - AN EASY ENTRY TO (R)-3-PYRROLIDINEACETIC ACID publication-title: SYNLETT contributor: fullname: CARDILLO, B – volume: 116 start-page: 9805 year: 1994 ident: WOS:A1994PN45200078 article-title: HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ENANTIOMERIC 2,3-DIHYDROXY THIOESTERS BY USING SIMILAR TYPES OF CHIRAL SOURCES DERIVED FROM L-PROLINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: KOBAYASHI, S – volume: 37 start-page: 8543 year: 1996 ident: WOS:A1996VU40500024 article-title: Nonenzymatic enantioselective acylation of racemic secondary alcohols catalyzed by a SnX(2)-chiral diamine complex publication-title: TETRAHEDRON LETTERS contributor: fullname: Oriyama, T – volume: 52 start-page: 1069 year: 1996 ident: WOS:A1996TL97400032 article-title: A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid publication-title: TETRAHEDRON contributor: fullname: Galeazzi, R – volume: 39 start-page: 3529 year: 1998 ident: WOS:000073490400047 article-title: Highly efficient catalytic asymmetric acylation of meso-1,2-diols with benzoyl chloride in the presence of a chiral diamine combined with Et3N publication-title: TETRAHEDRON LETTERS contributor: fullname: Oriyama, T – volume: 39 start-page: 817 year: 1996 ident: WOS:A1996TW13600003 article-title: Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Abreo, MA – volume: 70 start-page: 1687 year: 1997 ident: WOS:A1997XQ00100027 article-title: Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: Asami, M – volume: 41 start-page: 407 year: 1998 ident: WOS:000072030400001 article-title: Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Holladay, MW – volume: 39 start-page: 397 year: 1998 ident: WOS:000071241100016 article-title: Asymmetric acylation of meso-diols with benzoyl halide in the presence of a chiral diamine publication-title: TETRAHEDRON LETTERS contributor: fullname: Oriyama, T – start-page: 297 year: 1989 ident: WOS:A1989T380700034 article-title: ASYMMETRIC ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES PROMOTED BY THE COMBINED USE OF CHIRAL DIAMINE COORDINATED TIN(II) TRIFLATE AND TRIBUTYLTIN FLUORIDE publication-title: CHEMISTRY LETTERS contributor: fullname: KOBAYASHI, S – volume: 8 start-page: 133 year: 1997 ident: WOS:A1997WD63200021 article-title: From 3-aza-2-oxobicyclo[3.1.0]hexane to enantiopure disubstituted cyclopropane: A convenient approach to cis-2,3-methano-GABA publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Galeazzi, R – volume: 29 start-page: 59 year: 1996 ident: WOS:A1996WD20700001 article-title: New possibilities in organic synthesis publication-title: ALDRICHIMICA ACTA contributor: fullname: Mukaiyama, T – volume: 113 start-page: 4247 year: 1991 ident: WOS:A1991FN00500030 article-title: ASYMMETRIC ALDOL REACTION BETWEEN ACHIRAL SILYL ENOL ETHERS AND ACHIRAL ALDEHYDES BY USE OF A CHIRAL PROMOTER SYSTEM publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: KOBAYASHI, S – volume: 6 start-page: 2565 year: 1995 ident: WOS:A1995TD21600019 article-title: CHIRAL TIN(II) LEWIS ACID-MEDIATED ENANTIOSELECTIVE ALDOL REACTIONS - SYNTHESIS OF BOTH ENANTIOMERS USING SIMILAR TYPES OF CHIRAL SOURCES publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: KOBAYASHI, S – start-page: 265 year: 1999 ident: WOS:000079524500038 article-title: Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine publication-title: CHEMISTRY LETTERS contributor: fullname: Sano, T |
| SSID | ssj0008088 |
| Score | 1.5798554 |
| Snippet | New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8), (9), (14) and (15) were obtained through simple steps starting from chiral... |
| Source | Web of Science |
| SourceID | webofscience |
| SourceType | Enrichment Source Index Database |
| StartPage | 2463 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000083253400019 |
| Volume | 51 |
| WOS | 000083253400019 |
| WOSCitedRecordID | wos000083253400019 |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Na9tAEF2a9tBcQtukJGlSdMitbCJld6RVbsEkNS3uobiQW9gvEUOQjXEC9q_vzGotyyZQpxchC7ES-8Yzz8_zwdhZqoUjqLmVWnHpy5SbSgnuC22Losi1rUjvGPzK-3_kjzu4W7UnCNUlM3NuFy_WlfwPqngNcaUq2Vcg2y6KF_Ac8cUjIozHrTCm5ET7MKIae8FrPXnAXUeER_WYBkPPHyfzKQ3lcZTaHhXAp5p6-lvimX4yor9rmnSeb0gebQtSZKt9ypUZ2zllzrVA62e9pq5-xxCjF4vRWvbhYGwo6zao7q2OO_VNAdpgJTWE9gTLpLWof8Vg3XFRQgGnQeJdfxobyEa7SbveUUZn5uPHZmbIphcXQQe5pSCB76DyphXneq_sjRjWZhYGDiwuQcjAXnfYTqHI8WU_B22AVmkYR9q-fFO2SU-96DzzRSYSWMfwA9uLPxeS6wb7j-yNrz-x973llL599httIGlsIPmnDVwl13WysoBkzQKSpQUcsOHtzbDX53FOBq-zQs04uDz1pdNaIXsUDikpsmztwTlZ-FIaA1BUtrJgjXVgcUOgzMAIqIxwUl1-Zm_rce0PWQIitQrASk9iBbr73EJW-dJoXLQEOGJn3T25nzQdUe43dv2IZdvc1otd6Kn7wux4u6W_sN2VZZ6wdxV-lf0p8sKZ-RpQ_guiQmU_ |
| link.rule.ids | 786 |
| linkProvider | Clarivate |
| 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=New+chiral+3-naphthylaminomethylpyrrolidines%3A+An+unexpected+epimerisation+reaction&rft.jtitle=Heterocycles&rft.au=Fava%2C+C&rft.au=Galeazzi%2C+R&rft.au=Mobbili%2C+G&rft.au=Orena%2C+M&rft.date=1999-10-01&rft.pub=Elsevier&rft.issn=0385-5414&rft.volume=51&rft.issue=10&rft.spage=2463&rft.epage=2470&rft_id=info:doi/10.3987%2Fcom-99-8648&rft.externalDBID=n%2Fa&rft.externalDocID=000083253400019 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0385-5414&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0385-5414&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0385-5414&client=summon |