Alkylation of a Chiral Hydrazone by Means of Asymmetric Addition of Grignard Reagents to the Carbon-Nitrogen Double Bond
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概要
- 論文の詳細を見る
A chiral hydrazone, (E)-(S)-N'-benzylidene-N, 3-dimethyl-2-hydrazinobutanol (6), was synthesized from (S)-valinol. Compound 6 was reacted with Grignard reagents to give optically pure (2S, 1'S)-N, 3-dimethyl-N'-1'-phenylalkyl-2-hydrazinobutanols (7a and 7b). However, N'-2'-aryl-1'-phenylethyl-N, 3-dimethyl-2-hydrazinobutanols (7c and 7d) were each obtained as a mixture of two diastereomers. Nitrogen-nitrogen bonds of 7a and 7b were cleaved by hydrogenolysis to give (S)-1-phenylalkylamines (8a and 8b), and their absolute configurations and optical purities were confirmed. These reactions were assumed to proceed via the chelated sixmembered ring intermediates.
- 社団法人日本薬学会の論文
- 1983-12-25
著者
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高橋 浩
Faculty Of Pharmaceutical Science Hoshi University
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高橋 浩
Institute of Medicinal Chemistry, Hoshi University
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鈴木 雄二
Kaken Pharmaceutical Co., Ltd.
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鈴木 雄二
Hoshi College Of Pharmacy
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