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

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

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

Harvard

Clarke, C, Foussat, S, Fox, DJ, Pedersen, DS & Warren, S 2009, 'Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes', Organic & Biomolecular Chemistry, vol. 7, no. 7, pp. 1323-1328. https://doi.org/10.1039/b817433d

APA

Clarke, C., Foussat, S., Fox, D. J., Pedersen, D. S., & Warren, S. (2009). Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes. Organic & Biomolecular Chemistry, 7(7), 1323-1328. https://doi.org/10.1039/b817433d

Vancouver

Clarke C, Foussat S, Fox DJ, Pedersen DS, Warren S. Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes. Organic & Biomolecular Chemistry. 2009;7(7):1323-1328. https://doi.org/10.1039/b817433d

Author

Clarke, Celia ; Foussat, Stéphanie ; Fox, David J ; Pedersen, Daniel Sejer ; Warren, Stuart. / Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes. In: Organic & Biomolecular Chemistry. 2009 ; Vol. 7, No. 7. pp. 1323-1328.

Bibtex

@article{302930306d3a11de8bc9000ea68e967b,
title = "Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes",
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.",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Celia Clarke and St{\'e}phanie Foussat and Fox, {David J} and Pedersen, {Daniel Sejer} and Stuart Warren",
note = "Keywords: Boranes; Crystallography, X-Ray; Cyclopropanes; Models, Molecular; Molecular Structure; Oxides; Phosphines; Stereoisomerism",
year = "2009",
doi = "10.1039/b817433d",
language = "English",
volume = "7",
pages = "1323--1328",
journal = "Organic & Biomolecular Chemistry",
issn = "1470-4358",
publisher = "Royal Society of Chemistry",
number = "7",

}

RIS

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