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A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
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In this paper, the authors described a new method for the catalytic enantioselective reduction of ketones to chiral secondary alcohols, where the stoichiometric reagent in the reduction is borane and the catalyst is a chiral oxazaborolidine such as 1 (0.05-0.1 molfmol of ketone).Abstract:
We have recently described a new method for the catalytic enantioselective reduction of ketones to chiral secondary alcohols.' The stoichiometric reagent in the reduction is borane (usually 0.6 molfmol of ketone), and the catalyst is a chiral oxazaborolidine such as 1 (0.05-0.1 molfmol of ketone). Excellent enantioselectivities, easy recoverability of the chiral catalyst predecessor, near quantitative yields, short reaction times (a few minutes at 23 \"C), and predictability of the absolute configuration of the product contribute to the outstanding utility of this (CBS') process. This paper reports several subsequent developments in this area with respect to improved practicality and important applications. In contrast to 1 which is both air and moisture sensitive, the B-methylated oxazaborolidine 2 can be stored in closed containers at room temperature and weighed or transferred in air. Catalyst 2 is also much more easily prepared than 1. Reaction of (S)-read more
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Quantum chemical modeling of chiral catalysis. Part 9. On the aggregation reactions of borane and chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones
TL;DR: In this article, the behavior of oxazaborolidines, as they react with intermediates of the CBS reduction, was found to resemble that of ketones or Lewis basic solvents.
Journal ArticleDOI
Structural effects of the oxazaborolidine derived from L-threonine in the reduction of (trifluoroacetyl)biphenyl derivatives with catecholborane
TL;DR: In this paper, the reduction of trifluoroacetylbiphenyl derivatives with catecholborane as a stoichiometric reductant in the presence of the oxazaborolidine catalyst derived from L-threonine in dichloromethane-toluene at −90 °C proceeds to give the corresponding alcohols in high yields with high enantioselectivity.
Journal ArticleDOI
Application of Corey–Bakshi–Shibata, Corey–Kim, Corey–Seebach, Corey–Winter, Corey–Link, and Corey–Ganem–Gilman in organic and total synthesis
TL;DR: In the continuation of the authors' studies on the Corey-based reactions, this review tries to underscore the applications of Corey–Bakshi–Shibata, Corey–Kim oxidation,Corey–Winter, Corey-Link, and Corey–Ganem–Gilman reactions in synthetic organic chemistry and total synthesis of natural products.
Journal ArticleDOI
Kinetic investigation of the reduction of pinacolone by borane catalyzed by oxazaborolidines in THF. Hydride shift as rate determining step
TL;DR: In this paper, the authors studied the kinetics of the reduction of the ketone pinacolone (P) by borane (B) catalyzed by the oxazaborolidines (OAB) (S)-1-methyl-3,3-diphenylperhydropyrrolo[1,2-c][1,3,2]oxazaborolisine and (S]-2,4-dimethyl-3-3diphensyl-1, 3, 2-oxazabolidine have been
Journal ArticleDOI
Total synthesis of peumusolide A, NES non-antagonistic inhibitor for nuclear export of MEK
TL;DR: The first total synthesis of peumusolide A (1) has been achieved by combination of regio-and stereo-selective aluminum-mediated hydroiodination to 2-yn-1-ol and enantioselective reduction of 4-en-1/yn-3-one with the chiral oxazaborolidine as the key reactions as discussed by the authors.
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Book
Molybdenum and Molybdenum-Containing Enzymes
TL;DR: In this article, a few moment to read a book even only few pages is recommended, even if it is not obligation and force for everybody, reading book becomes a choice of your different characteristics.
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Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.
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