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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 20
151
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Original Articles

Unusual Course of the Reaction of Allyl Phosphine Oxides with the Grundmann Ketone

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Pages 2943-2954 | Received 25 Feb 2014, Published online: 08 Aug 2014
 

Abstract

This article describes efficient preparation of isomeric allyl phosphine oxides possessing a protected cyclohexanediol fragment. Their base-catalyzed interconversions are examined and reactions with the Grundmann ketone provide an adduct containing the rearranged vinyl phosphine oxide moiety, instead of 19-norvitamin D3 analogs, the expected products of the Horner–Wittig process.

GRAPHICAL ABSTRACT

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