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Synthesis 2011(22): 3661-3668
DOI: 10.1055/s-0030-1260232
DOI: 10.1055/s-0030-1260232
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSequential One-Pot Isomerization-Wittig Olefination-Hydrogenation
Further Information
Received
6 July 2011
Publication Date:
20 September 2011 (online)
Publication History
Publication Date:
20 September 2011 (online)
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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