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Titolo:
Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions
Autore:
Barberis, C; Voyer, N; Roby, J; Chenard, S; Tremblay, M; Labrie, P;
Indirizzi:
Univ Laval, Dept Chim, St Foy, PQ G1K 7P4, Canada Univ Laval St Foy PQ Canada G1K 7P4 Dept Chim, St Foy, PQ G1K 7P4, Canada Univ Laval, Fac Sci & Genie, CREFSIP, St Foy, PQ G1K 7P4, Canada Univ Laval St Foy PQ Canada G1K 7P4 , CREFSIP, St Foy, PQ G1K 7P4, Canada
Titolo Testata:
TETRAHEDRON
fascicolo: 15, volume: 57, anno: 2001,
pagine: 2965 - 2972
SICI:
0040-4020(20010409)57:15<2965:RATNPD>2.0.ZU;2-Z
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE SYNTHESIS; AMINO-ACIDS; ASYMMETRIC SYNTHESES; ALPHA-LITHIATION; GAMMA-ARYL; BETA-ARYL; (-)-SPARTEINE; SUBSTITUTION; N-BOC-N-(P-METHOXYPHENYL)BENZYLAMINE; DEPROTONATION;
Keywords:
enantioselective deprotonation; (-)-sparteine; organolithium; carboxylation; phenylglycine;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Voyer, N Univ Laval, Dept Chim, St Foy, PQ G1K 7P4, Canada Univ Laval St Foy PQ Canada G1K 7P4 , St Foy, PQ G1K 7P4, Canada
Citazione:
C. Barberis et al., "Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions", TETRAHEDRON, 57(15), 2001, pp. 2965-2972

Abstract

We report a novel and efficient method for the enantioselective synthesis of N-Boc protected phenylglycines. Yields and enantiomeric ratios vary widely depending on the nature of the solvent, the substrate and on the method of forming the chiral complex. Results show that the major reaction pathwayis an enantioselective deprotonation/substitution process. The enantioselectivity appears to be limited by the chiral discrimination ability of the s-BuLi-(-)-sparteine complex. The synthetic method described is one of the shortest route to useful enantioenriched N-Boc phenylglycine derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/01/20 alle ore 15:40:20