Enantioselective Evans-Tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate

Tomonori Ichibakase; Masato Nakatsu; Makoto Nakajima

doi:10.3390/molecules16065008

Enantioselective Evans-Tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate

Molecules. 2011 Jun 17;16(6):5008-19. doi: 10.3390/molecules16065008.

Authors

Tomonori Ichibakase¹, Masato Nakatsu, Makoto Nakajima

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, Japan.

Abstract

Lithium diphenylbinaphtholate catalyzed the enantioselective Evans-Tishchenko reduction of achiral β-hydroxyketones to afford monoacyl-protected 1,3-diols with high stereoselectivities. In the reaction of racemic β-hydroxyketones, kinetic optical resolution occurred in a highly stereoselective manner.

MeSH terms

Catalysis
Ketones / chemistry*
Ketones / metabolism*
Kinetics
Lithium / chemistry*
Nuclear Magnetic Resonance, Biomolecular
Oxidation-Reduction
Stereoisomerism

Substances

Ketones
Lithium