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
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
收藏
页码:1051 / 1055
页数:5
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