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Issue 7, 2009
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Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes

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Abstract

The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from β-alkyl, γ-benzoyl phosphine oxides via a three-step cascade reaction incorporating an acyl transfer, phosphinoyl transfer and cyclisation to form the cyclopropane. Using Evans’ chiral oxazolidinone auxiliary and by masking the phosphine oxide moiety as a phosphine borane we have extended the method to the synthesis of enantiomerically-enriched trans-disubstituted cyclopropyl ketones.

Graphical abstract: Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes

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Article information


Submitted
03 Oct 2008
Accepted
30 Oct 2008
First published
12 Dec 2008

Org. Biomol. Chem., 2009,7, 1323-1328
Article type
Paper

Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes

C. Clarke, S. Foussat, D. J. Fox, D. S. Pedersen and S. Warren, Org. Biomol. Chem., 2009, 7, 1323
DOI: 10.1039/B817433D

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