Asymmetric synthesis of bicyclic α-amino acids by a Diels-Alder reaction to a new chiral α,β-didehydroalanine derivative

被引：20

作者：

Chinchilla, R

Falvello, LR

Galindo, N

Nájera, C

机构：

[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Zaragoza, Fac Ciencias, Inst Ciencia Mat Aragon, Dept Quim Inorgan,CSIC, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(99)00061-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new chiral cyclic alpha,beta-didehydroalanine derivative, (6S)-6-isopropyl-3-methylene-5-phenyl-3,6,dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a reactive dienophile ire highly diastereoselective Diels-Alder reactions with cyclopenta- and cyclohexadiene. The major cycloadducts have been isolated and hydrolyzed to afford enantiomerically pure (-)-endo-2-aminobicyclo[2.2.1]heptane-2- and exo-2-aminobicyclo[2.2.2]octane-2-carboxylic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：821 / 825

页数：5

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