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Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921
Janak Singh1, David R Kronenthal, Mark Schwinden
1Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543, USA. janak.singh@bms.com
Organic Letters
|August 15, 2003
Abstract:
[reaction: see text] An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-alpha-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted to racemic alpha-aminoazepinone 15b, which was transformed to 6b by a practical dynamic resolution.