有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
β-ラクタム環構築における異なる金属種を用いる立体化学のスイッチング
藤澤 有清水 真
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ジャーナル フリー

1995 年 53 巻 6 号 p. 518-529

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The importance of the stereodivergent synthesis of both enantiomers of β-lactams is ever increasing in connection with the structure-activity relationship study and the development of new derivatives in the β-lactam antibiotics. In this account stereocontrol at the C-3 and C-4 carbons of β-lactams using metal ester enolate-imine condensation reactions is discussed. The addition of an achiral ester enolate with a chiral imine possessing a dioxolane ring derived from (2S, 3S)-1, 4-dimethoxy-2, 3-butanediol as a chiral auxiliary is presented, in which 4-monosubstituted, 3, 4-disubstituted, and 3, 3, 4-trisubstituted β-lactams are prepared in a highly stereodivergent manner simply by switching metal ester enolate species. The application to the stereoselective synthesis of 1β-methylcarbapenem from 4-monosubstituted β-lactam is conducted by the use of selective hydrogenation reaction as a crucial step. The addition of an achiral ester enolate with a chiral imine having an auxiliary derived from phenylglycine at the nitrogen and the reaction of a chiral ester possessing arylsulfinyl group as an auxiliary at the α-position to the carbonyl with an achiral imine are also described for the stereodivergent synthesis of each of β-lactams from a single chiral source.

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