Facile approach towards the synthesis of homochiral functionalised alcohols from 4-O-[(tert)-butyldimethylsilyl]-2,3-O-cyclohexylidene-L-threose of (L)-(+)-tartaric acid origin

被引：17

作者：

Chattopadhyay, A ^{[1
]}

Dhotare, B ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Mumbai 400085, India

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(98)00282-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(L)-(+)-Diethyl tartarate 2 has been transformed into the aldehyde 6. Grignard additions to 6 take place with moderate diastereoselectivity giving predominant formation of the anti products 8a-e. However, in each case the diastereoalcohols are easily separable by column chromatography giving rise to the formation of a series of functionalised homochiral alcohols 7 and 8. On the other hand Zn mediated allylation and propargylation of 6 in the presence of water proceeded efficiently with almost absolute (>99%) stereoselective formation of versatile functionalised homoallylic 8d and homopropargylic 8e alcohols respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2715 / 2723

页数：9

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