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Paper

Org. Biomol. Chem., 2009, 7, 1323 - 1328, DOI: 10.1039/b817433d

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

Celia Clarke, Stéphanie Foussat, David J. Fox, Daniel Sejer Pedersen and Stuart Warren

The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from -alkyl, -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.

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