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Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes
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Clarke, Celia, Foussat, Stephanie, Fox, David J., Pedersen, Daniel Sejer and Warren, Stuart (2009) Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes. Organic & Biomolecular Chemistry, Vol.7 (No.7). pp. 1323-1328. doi:10.1039/b817433d ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/b817433d
Abstract
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.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||
Publisher: | Royal Society of Chemistry | ||||
ISSN: | 1477-0520 | ||||
Official Date: | 2009 | ||||
Dates: |
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Volume: | Vol.7 | ||||
Number: | No.7 | ||||
Number of Pages: | 6 | ||||
Page Range: | pp. 1323-1328 | ||||
DOI: | 10.1039/b817433d | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | Torben & Alice Frimodts Fond, Brodrene Hartmanns Fond, Direktor Ib Henriksens Fond |
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