ORGN 456 |
Asymmetric reduction with aminoindanol based oxazaborolidines
| Nathan J. Gilmore and Simon Jones. Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, United Kingdom |
The importance of solvent effects and hydride source in the reduction of a variety of prochiral ketones with oxazaborolidine catalysts 1 and 2 derived from cis-1-amino-2-indanol have been investigated. Catalyst 2 gave comparable or improved enantioselectivity, in addition to eliminating the purification / isolation required with the B-Me catalyst 1. Studies of these catalyst systems show 10% catalyst loading is preferred, however catalyst 2 shows slightly superior catalyst endurance. Introduction of enantiomerically pure alcohols as a substitute for the B-OMe or B-Me group allows investigation of double stereodifferentiation in the catalytic reduction. Studies examining possible dynamic kinetic resolution of a-bromopropiophenone is also discussed.  |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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