Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes
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Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes. / Clarke, Celia; Foussat, Stéphanie; Fox, David J; Pedersen, Daniel Sejer; Warren, Stuart.
In: Organic & Biomolecular Chemistry, Vol. 7, No. 7, 2009, p. 1323-1328.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes
AU - Clarke, Celia
AU - Foussat, Stéphanie
AU - Fox, David J
AU - Pedersen, Daniel Sejer
AU - Warren, Stuart
N1 - Keywords: Boranes; Crystallography, X-Ray; Cyclopropanes; Models, Molecular; Molecular Structure; Oxides; Phosphines; Stereoisomerism
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1039/b817433d
DO - 10.1039/b817433d
M3 - Journal article
C2 - 19300816
VL - 7
SP - 1323
EP - 1328
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1470-4358
IS - 7
ER -
ID: 13087504