Chiral epoxides as a source of chiral beta-oxidofunctionalised organolithium compounds: Reaction with electrophiles

被引：33

作者：

Bachki, A ^{[1
]}

Foubelo, F ^{[1
]}

Yus, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,ALICANTE 03080,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 10期

关键词：

D O I：

10.1016/0957-4166(96)00390-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reductive opening of chiral epoxides 1, 4, 7 and 11 with lithium powder and a catalytic amount of DTBB (5 mol %) in THF at -78 degrees C, followed by treatment with different electrophiles [Bu(t)CHO, PhCHO, (CH2)(5)CO, PhCOMe, CO2, H2O, D2O,] at the same temperature leads, after hydrolysis with water, to enantiomerically pure functionalised alcohols 3, 6, 9, 10 and 13. Monoprotected diols 6 and 10 give 1,2,4-triols 14 after treatment under acidic conditions in methanol, in almost quantitative yield. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2997 / 3008

页数：12

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