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

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

doi:10.1039/B817433D

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Organic & Biomolecular Chemistry

Issue 7, 2009

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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

Org. Biomol. Chem., 2009, 7, 1323-1328

DOI: 10.1039/B817433D
Received 03 Oct 2008, Accepted 30 Oct 2008
First published on the web 12 Dec 2008

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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.

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Asymmetric synthesis of trans-disubstituted cyclopropanesusing phosphine oxides and phosphine boranes
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Celia Clarke
Stéphanie Foussat
David J. Fox
Daniel Sejer Pedersen
Stuart Warren

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Organic & Biomolecular Chemistry

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

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