A Twist on Facial Selectivity of Hydride Reductions of Cyclic Ketones: Twist-Boat Conformers in Cyclohexanone, Piperidone, and Tropinone Reactions
Author:
Affiliation:
1. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
2. Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, United States
Funder
National Institute of General Medical Sciences
Publisher
American Chemical Society (ACS)
Subject
Organic Chemistry
Link
https://pubs.acs.org/doi/pdf/10.1021/jo5022635
Reference50 articles.
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2. bGreeves, N.Comprehensive Organic Synthesis;Trost, B. M.; Fleming, I., Eds.Pergamon Press:Oxford, 1991; Vol.8, p1.
3. Reduction with Metal Hydrides. VIII. Reductions of Ketones and Epimerization of Alcohols with Lithium Aluminum Hydride-Aluminum Chloride1,2
4. Lithium tri-sec-butylborohydride. New reagent for the reduction of cyclic and bicyclic ketones with super stereoselectivity. Remarkably simple and practical procedure for the conversion of ketones to alcohols in exceptionally high stereochemical purity
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