Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Ki Po Jang; Gerri E. Hutson; Ryne C. Johnston; Elizabeth O. McCusker; Paul H.Y. Cheong; Karl A. Scheidt

doi:10.1021/ja410932t

Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Ki Po Jang, Gerri E. Hutson, Ryne C. Johnston, Elizabeth O. McCusker, Paul H.Y. Cheong, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

81 Scopus citations

Abstract

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C₁-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

Original language	English (US)
Pages (from-to)	76-79
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	1
DOIs	https://doi.org/10.1021/ja410932t
State	Published - Jan 8 2014

ASJC Scopus subject areas

Chemistry(all)
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja410932t

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abstract = "A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.",

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AU - McCusker, Elizabeth O.

AU - Cheong, Paul H.Y.

AU - Scheidt, Karl A.

PY - 2014/1/8

Y1 - 2014/1/8

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Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Abstract

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CCDC 957104: Experimental Crystal Structure Determination

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Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Abstract

ASJC Scopus subject areas

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CCDC 957104: Experimental Crystal Structure Determination

Cite this