Journal of Organic Chemistry p. 4324 - 4330 (1995)
Update date:2022-08-29
Topics:
Tschaen, David M.
Abramson, Lee
Cai, Dongwei
Desmond, Richard
Dolling, Ulf-H.
et al.
Described herein is an efficient asymmetric synthesis of the potent antiarrhthymia agent MK-0499.The route is convergent and is highlighted by two stereoselective reactions.A ruthenium-catalyzed, enantioselective hydrogenation of an enamide was developed for the preparation of the key amine intermediate.Oxazaborolidine-mediated ketone reduction was utilized to establish the alcohol stereochemistry.Optimization of this chemistry led to an IPA modified reduction method which provides enhanced stereoselectivity.
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