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

Org Lett. 2009 Dec 17;11(24):5714-6. doi: 10.1021/ol902507x.

Authors

Jun-Feng Zhao¹, Teguh-Budiono W Tjan, Boon-Hong Tan, Teck-Peng Loh

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

PMID: 19911807
DOI: 10.1021/ol902507x

Abstract

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).