Chiral (Z)-α,β-didehydroamino acid derivatives from a new chiral glycine equivalent with a 1,2,3,6-tetrahydropyrazin-2-one structure:: applications to the synthesis of 1-aminocyclopropanecarboxylic acids and bicyclic α-amino acids

被引：15

作者：

Abellán, T ^{[1
]}

Nájera, C ^{[1
]}

Sansano, JM ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)00023-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The new chiral glycine equivalent 9, easily obtained from(+)-alpha-aminoisovalerophenone and glycine, afforded chiral (Z)-alpha,beta-didehydroamino acid (DDAA) derivatives 13 and 14 with a 1,2,3,6-tetrahydropyrazin-2-one structure. Compounds 13 and 14 were synthesised by reaction of 9 with Eschenmoser's salt and by condensation reactions with aldehydes or acetone under PTC conditions, respectively. The diastereoselective cyclopropanation of 14, followed by hydrolysis, furnished (-)-allo-norcoronamic acid with high ee, whilst diastereoselective Diels-Alder reaction of dienophile 13 and cyclopentadiene afforded, after double bond hydrogenation and hydrolysis, (-)-2-aminonorbornane-2-carboxylic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1051 / 1055

页数：5

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