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A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
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TLDR
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
Citations
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Quantum chemical modeling of chiral catalysis. On the mechanism of catalytic enantioselective reduction of carbonyl compounds by chiral oxazaborolidines
TL;DR: In this article, the energy of two model systems of oxazaborolidine type of chiral reduction catalysts (CBS reduction), their borane adducts, and formaldehyde complexes of the BN bond were calculated by using ab initio molecular orbital methods.
Journal ArticleDOI
A Strategy for Total Synthesis of Complex Cardenolides.
Journal ArticleDOI
Catalytic enantioselective synthesis of a key intermediate for the synthesis of prostanoids
TL;DR: In this article, a route has been demonstrated for the enantioselective synthesis of prostanoids from achiral starting materials by the use of chiral catalysts of the molecular robot class.
Journal ArticleDOI
Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Functionalized γ-Hydroxy Amides
TL;DR: The combination of enzymatic kinetic resolution with a ruthenium-catalyzed racemization led to a dynamic kinetic resolution of racemic gamma-hydroxy amides 1 and the synthetic utility was illustrated by the practical synthesis of the versatile intermediate gamma-lactone (R)-5-methyltetrahydrofuran-2-one.
Journal ArticleDOI
Evolution of a series of non-quinoline leukotriene D4 receptor antagonist; synthesis and sar of benzothiazoles and thiazoles substituted benzyl alcohols as potent LTD4 antagonists
Lau Cheuk-Kun,Claude Dufresne,Yves Gareau,Robert Zamboni,Marc Labelle,Robert N. Young,Kathleen M. Metters,C. Rochette,Nicole Sawyer,Deborah Slipetz,L. Charette,Thomas R. Jones,M. McAuliffe,C. S. Mcfarlane,Anthony W. Ford-Hutchinson +14 more
TL;DR: In this paper, a series of potent and orally active LTD4 receptor antagonists are described. But the synthesis and structure activity relationships of this series of compounds are described only in terms of structure and function.
References
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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.
Related Papers (5)
Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.
E. J. Corey,Christopher J. Helal +1 more