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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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Total synthesis of dysidiolide
E. J. Corey and,Bryan E. Roberts +1 more
TL;DR: The cdc25A protein phosphatase inhibitor dysidiolide has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product.
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Resolution of racemic carboxylic acid derivatives by Ti-TADDOLate mediated esterification reactions—A general method for the preparation of enantiopure compounds
Dieter Seebach,Georg Jaeschke,Konstanze Gottwald,Keiji Matsuda,Roberto Formisano,David A Chaplin,Matthias Breuning,Gerhard Bringmann +7 more
TL;DR: In this paper, the Lewis-acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates 1 to cyclic carboxylic acid derivatives is described.
Journal ArticleDOI
Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction
E. J. Corey,Christopher J. Helal +1 more
TL;DR: In this article, a new process has been developed for the highly enantioselective catalytic reduction of 2-aroylpyridines and successfully applied to the synthesis of (S)-carbinoxamine (1 ), a therapeutically important histamine H 1 antagonist.
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Recent progress in the chemistry of acylsilanes, a review
Pier F. Cirillo,James S. Panek +1 more
TL;DR: A review of progress in the CHEMISTRY of Ivory Coast can be found in this article, with a focus on the present progress in organic preparation and procedures in Ivory Coast.
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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