STEREOSELECTIVE [2,3]-SIGMATROPIC WITTIG REARRANGEMENT OF BENZYL ETHERS DERIVED FROM VINYLCUPRATE ADDUCTS OF (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE

被引：4
作者：
METZ, P
SCHOOP, A
机构：
[1] Organisch-Chemisches Institut der Universität Münster., D-48149 Münster
来源：
TETRAHEDRON | 1995年 / 51卷 / 33期
关键词：
D O I：
10.1016/0040-4020(95)00497-V
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Allyl alcohols 2 prepared by addition of lithium vinylcuprates to (R)-2,3-O-isopropylideneglyceraldehyde (1) are converted to 3,4,5-trimethoxybenzyl ethers 3 by a one-pot desilylation/alkylation. After deprotonation using potassium t-butoxide/t-butyllithium/N,N,N',N'-tetramethylethylenediamine in t-butyl methyl ether at -78 degrees C, substrates 3 undergo a [2,3]-sigmatropic Wittig rearrangement with complete 1,3-chirality transfer and good simple diastereoselectivity to give homoallyl alcohols 5 as the major products.
引用
收藏
页码：9023 / 9030
页数：8
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