Highly enantioselective ketone-ene reactions of trifluoropyruvate: Significant counterion effect of the in(III)-pybox complex

Jun Feng Zhao; Teguh Budiono W. Tjan; Boon Hong Tan; Teck Peng Loh

doi:10.1021/ol902507x

Highly enantioselective ketone-ene reactions of trifluoropyruvate: Significant counterion effect of the in(III)-pybox complex

Jun Feng Zhao, Teguh Budiono W. Tjan, Boon Hong Tan, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

38 Citations (Scopus)

Abstract

[Chemical Equation Presented] A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

Original language	English
Pages (from-to)	5714-5716
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	24
DOIs	https://doi.org/10.1021/ol902507x
Publication status	Published - Dec 17 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol902507x

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abstract = "[Chemical Equation Presented] A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).",

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T2 - Significant counterion effect of the in(III)-pybox complex

AU - Zhao, Jun Feng

AU - Tjan, Teguh Budiono W.

AU - Tan, Boon Hong

AU - Loh, Teck Peng

PY - 2009/12/17

Y1 - 2009/12/17

N2 - [Chemical Equation Presented] A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

AB - [Chemical Equation Presented] A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

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Highly enantioselective ketone-ene reactions of trifluoropyruvate: Significant counterion effect of the in(III)-pybox complex

Abstract

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