Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes
Research output: Contribution to journal › Journal article › Research › peer-review
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 language | English |
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Journal | Organic & Biomolecular Chemistry |
Volume | 7 |
Issue number | 7 |
Pages (from-to) | 1323-1328 |
ISSN | 1477-0520 |
DOIs | |
Publication status | Published - 2009 |
Bibliographical note
Keywords: Boranes; Crystallography, X-Ray; Cyclopropanes; Models, Molecular; Molecular Structure; Oxides; Phosphines; Stereoisomerism
- Former Faculty of Pharmaceutical Sciences
Research areas
ID: 13087504