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Synthetic studies on carbapenem antibiotics from penicillins. IV. Stereoselective kinetic protonation of a chiral azetidinone enolate
Authors:Hideo Hirai  Kozo Sawada  Matsuhiko Aratani  Masashi Hashimoto
Institution:1. Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd., 2-1-6 Kashima, Yodogawa-ku, Osaka 532, Japan;2. Central Laboratories Fujisawa Pharmaceutical Co., Ltd., 2-1-6 Kashima, Yodogawa-ku, Osaka 532, Japan
Abstract:A stereoselective kinetic protonation of the azetidinone enolate B was studied and an efficient synthesis of2(cis) was achieved via aldol reaction of 5 with acetone followed by the kinetic protonation with Ph3SnH as proton source.
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