RING-OPENING OF GLYCIDYL DERIVATIVES BY SILANES MEDIATED BY TI(O-ISO-PR)4 OR AL(O-ISO-PR)3 - ACCESS TO VERSATILE C3 BUILDING-BLOCKS

被引:10
作者
SUTOWARDOYO, KI
SINOU, D
机构
[1] Laboratoire de Synthèse Asymétrique, Unité Associée au CNRS, af]Université Claude Bernard Lyon I, 69622 Villeurbanne Cédex
关键词
D O I
10.1016/S0957-4166(00)82168-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ring-opening of chiral glycidol or glycidyl tosylate by Me3SiN3 or Me3SiCN catalyzed by Ti(O-i-Pr)4 or Al(O-i-Pr)3 occured in a regiospecific manner and with very high stereoselectivity, leading to new trifunctionalized chiral building blocks. The enantiomeric excess of the ring-opened products was 90-95 %, as determined by H-1 NMR of the Mosher ester derivatives, indicating that there was not significant loss of optical purity during the ring-opening. This methodology was applied for the one-pot synthesis of (R)-1-azido-3-naphthyloxy-2-hydroxypropane in 94 % ee, a precursor of analogs of propanolol.
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页码:437 / 444
页数:8
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