Sequential One-Pot Isomerization-Wittig Olefination-Hydrogenation

被引：4

作者：

Sabitha, Gowravaram ^{[1
]}

Nayak, Sambit ^{[1
]}

Bhikshapathi, M. ^{[1
]}

Chittapragada, Maruthi ^{[1
]}

Yadav, J. S. ^{[1
,2
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500607, Andhra Pradesh, India

[2] King Saud Univ, Bee Res Chair, Coll Food & Agr Sci, Riyadh, Saudi Arabia

来源：

SYNTHESIS-STUTTGART | 2011年 / 22期

关键词：

isomerization; Wittig olefination; hydrogenation; oxa-Michael reaction; aldehydes; CONFIGURATION; MACROLIDE;

D O I：

10.1055/s-0030-1260232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary allylic alcohols are isomerized to aldehydes in the presence of Pd(OH)(2) and homologated to alpha,beta-unsaturated carbonyl derivatives in one-pot by addition of stabilized Wittig ylides in a sequential fashion. When the reaction was prolonged by addition of more catalyst, a hydrogenation step succeeds the Wittig olefination. In addition, sequential isomerization-Wittig olefination-oxa-Michael addition reaction provides tetrahydropyran with high diastereoselectivity.

引用

页码：3661 / 3668

页数：8

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