Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids from a new chiral glycine equivalent with 3,6-dihydro-2H-1,4-oxazin-2-one structure

被引：22

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

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00244-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Condensation of the new chiral glycine equivalent 10 with aldehydes at room temperature in the presence of K2CO3 under solid-liquid phase-transfer-catalysed conditions afforded stereoselectively new chiral (Z)-alpha,beta-didehydroamino acid (DDAA) derivatives with oxazinone structure 14. These systems have been used in diastereoselective cyclopropanation reactions for the synthesis of enantiomerically pure 1-aminocyclopropanecarboxylic acids (ACCs) such as (-)-allo-norcoronamic and (-)-allo-coronamic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2223 / 2227

页数：5

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[1] ASYMMETRIC-SYNTHESIS BY THE CN(R,S) METHOD .19. ASYMMETRIC-SYNTHESIS OF 2,3-METHANOHOMOSERINE - A GENERAL-APPROACH TO CHIRAL 2-SUBSTITUTED CYCLOPROPANE AMINO-ACIDS [J].