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

Research output: Contribution to journalJournal articleResearchpeer-review

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

The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from beta-alkyl, gamma-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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume7
Issue number7
Pages (from-to)1323-1328
ISSN1477-0520
DOIs
Publication statusPublished - 2009

Bibliographical note

Keywords: Boranes; Crystallography, X-Ray; Cyclopropanes; Models, Molecular; Molecular Structure; Oxides; Phosphines; Stereoisomerism

ID: 13087504