Journal ArticleDOI
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
Citations
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Journal ArticleDOI
Chiral ligand derived from (1S,2R)-norephedrine as a catalyst for enantioselective prochiral ketone reduction
TL;DR: Chiral oxazaborolidines derived from (1 S,2 R )-(+)-norephedrine and substituted salicylaldehydes were employed in the asymmetric reduction of prochiral ketones using borane dimethyl sulfide as a reducing agent as discussed by the authors.
Book ChapterDOI
Chapter 3 - The Total Synthesis of (-)-Arisugacin A.
Richard P. Hsung,Kevin P. Cole +1 more
TL;DR: Arisugacin is a potent and selective inhibitor of acyltransferase (AChE) with an IC 50 of 1 nM and is well-selective for AChE because >18 μM is required to inhibit butyrylcholinesterase [BuChE].
Journal ArticleDOI
Inhibiting prolyl isomerase activity by hybrid organic–inorganic molecules containing rhodium(II) fragments
TL;DR: A small molecule containing a rhodium(II) tetracarboxylate fragment is shown to be a potent inhibitor of the prolyl isomerase FKBP12.
Journal ArticleDOI
Synthesis and evaluation of 2,3-dinorprostaglandins: Dinor-PGD1 and 13-epi-dinor-PGD1 are peroxisome proliferator-activated receptor α/γ dual agonists.
TL;DR: In this paper, the authors synthesized dinor-PGs that may possibly be derived from γ-linolenic acid (GLA) and examined their activities towards peroxisome proliferator-activated receptors (PPARs).
Journal ArticleDOI
Stereoselective synthesis of C3–C17 and C18–C34 subunits of bullatanocin utilizing α-chloro sulfide intermediates
TL;DR: In this paper, a convergent synthesis of bullatanocin is envisaged by the union of C18−C34, C3−C17 and the butenolide subunits.
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