Synthetic Studies on Optically Active β-Lactams. II. : Asymmetric Synthesis of β-Lactams by [2+2]Cyclocondensation Using Heterocyclic Compounds Derived from L-(+)-Tartaric Acid, (S)- or (R)-Glutamic Acid, and (S)-Serine as Chiral Auxiliaries
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概要
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Asymmetric synthesis of β-lactams by the [2+2]cyclocondensation of an imine (7) to chiral ketene species (2b, 4b, and 6c) bearing heterocycles derived from L-(+)-tartaric acid, (S)-glutamic acid, and (S)-serine was carried out. The reaction of 2b with 7 gave the trans-β-lactams with 74% diastereomeric excess, and cis-β-lactams were predominantly formed with high diastereomeric purity (up to 96%) when 4b and 6c were employed. Asymmetric synthesis of (3S, 4S)- and (3R, 4R)-1-benzyl-3[(benzyloxycarbonyl)amino]-4-hydroxymethyl-2-azetidinones (26 and 30g) using (R)-4b as a ketene species and the chiral imine (21) prepared from L-(+)-tartaric acid was also achieved.
- 公益社団法人日本薬学会の論文
- 1990-06-25
著者
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伊古田 暢夫
放射線医学総合研究所重粒子医科学センター
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伊古田 暢夫
National Institute of Padiological Sciences
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伊古田 暢夫
National Institute Of Radiological Sciences
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