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Synthesis 2011(22): 3661-3668  
DOI: 10.1055/s-0030-1260232
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sequential One-Pot Isomerization-Wittig Olefination-Hydrogenation

Gowravaram Sabitha*a, Sambit Nayaka, M. Bhikshapathia, Maruthi Chittapragadaa, J. S. Yadava,b
a Division of Organic Chemistry I, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
b Bee Research Chair, College of Food and Agriculture Science, King Saud University, Riyadh, Saudi Arabia
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Publication History

Received 6 July 2011
Publication Date:
20 September 2011 (online)

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Abstract

Primary allylic alcohols are isomerized to aldehydes in the presence of Pd(OH)2 and homologated to α,β-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.

Key words

isomerization - Wittig olefination - hydrogenation - oxa-Michael reaction - aldehydes

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