Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines

被引：18

作者：

Sano, S

Miwa, T

Liu, XK

Ishii, T

Takehisa, T

Shiro, M

Nagao, Y

机构：

[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(98)00371-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diastereoselective aldol-type reactions of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazine-carboxylate (5S)-3 with achiral aldehydes 8a-d was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine and MgBr2-triethylamine. The reaction with Sn(II) between (5S)-3 and aliphatic aldehydes 8a,b proved to be quite different from that with Mg(II). On the other hand, Sn(II)- or Mg(II)-mediated aldol-type reactions of (5S)-3 with benzaldehyde Sc and 3-methyl-2-butenal 8d each afforded the same diastereomer as the major product. These aldol products were each converted to the corresponding alpha-substituted serines 6 and 7 as enantiomerically pure compounds. (C) 1998 Elsevier Science Ltd. AII rights reserved.

引用

页码：3615 / 3618

页数：4

共 5 条

[1] Diastereoselective alkylation of a newly designed bislactim ether towards the asymmetric synthesis of α-alkylated serines [J].