Alkylation of chiral 2-(aminomethyl)oxazolines

被引：7

作者：

LeBail, M

Aitken, DJ

Vergne, F

Husson, HP

机构：

[1] Laboratoire de Chimie Thérapeutique Associé au CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes (Paris V), 75270 Paris Cedex 06

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 11期

关键词：

D O I：

10.1039/a608030h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral 2-(aminomethyl)oxazolines 3 and 7, in which the heterocycle is derived from (R)-phenylglycinol, ale synthesized and studied in alkylation reactions involving strong base and alkyl halides. The tertiary amine derivative 3 is alkylated efficiently at the alpha-carbon centre with no stereochemical induction, while the tertiary carbamate 7 is alkylated in moderate yield and reasonable diastereomeric excess. The stereochemical control observed in the latter case can be explained by the preferred formation of an E-enolate during the deprotonation step by prior complexation of the carbamate carbonyl group to the base.

引用

页码：1681 / 1689

页数：9

共 46 条

[1] TOTAL SYNTHESIS OF (-)-BISTATRAMIDE-C [J].

AGUILAR, E ;

MEYERS, AI .

TETRAHEDRON LETTERS, 1994, 35 (16) :2477-2480

[2]

AITKEN DJ, 1993, SYNLETT, P599

[3] Asymmetric addition of organolithium reagents to prochiral arene tricarbonylchromium complexes [J].

Amurrio, D ;

Khan, K ;

Kundig, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2258-2259

[4] CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS [J].

ARNOLD, LD ;

DROVER, JCG ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4649-4659

[5]

BAKSHEEV AN, 1952, J GEN CHEM USSR, V22, P2077

[6]

Bodanszky M., 1993, PRINCIPLES PEPTIDE S, V2nd

[7] CYCLOPEPTIDES FROM ASCIDIANS - TOTAL SYNTHESIS OF LISSOCLINAMIDE-4, AND A GENERAL STRATEGY FOR THE SYNTHESIS OF CHIRAL THIAZOLINE-CONTAINING MACROCYCLIC PEPTIDES [J].

BODEN, CDJ ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1995, 36 (34) :6153-6156

[8] PREPARATION OF FUNCTIONALIZED OXAZOLINES [J].

BRETON, P ;

ANDREBARRES, C ;

LANGLOIS, Y .

SYNTHETIC COMMUNICATIONS, 1992, 22 (17) :2543-2554

[9]

BRETON P, 1992, THESIS U PARIS SUD O

[10] A NOVEL PREPARATIVE METHOD FOR ALPHA,BETA-UNSATURATED OXAZOLINES VIA ALPHA-PHENYLTHIOOXAZOLINES [J].

CLINET, JC ;

BALAVOINE, G .

TETRAHEDRON LETTERS, 1987, 28 (45) :5509-5512

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