An Asymmetric Synthesis of 2-Substituted Piperidines through Ozonolysis of Cyclopentenes and Reductive Aminocyclization(Organic Chemistry)
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概要
- 論文の詳細を見る
By the action of ozone, sodium cyanoborohydride and the optically active benzylic amines 2, the 1-substituted cyclopentenes 1, 5 and 9 were converted to a diastereoisomeric mixture of 1,2-disubstituted piperidines (3, 6 and 10), respectively. Hydrogenation of these compounds and the following work-up yielded optically active 2-alkylpiperidines (4, up to 68%e.e.), pipecolic acid (7, 84%e.e.) and 2-(hydroxymethyl)piperidine (11, up to 85%e.e.). Chromatographic separation of the major isomers of 3b and 6 enabled optically pure coniine (4b) and pipecolic acid (7) to be prepared, respectively.
- 社団法人日本農芸化学会の論文
- 1986-12-23
著者
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Hamada Masayuki
Department of Intern. Med. Mie Univ. School of Med.
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HAYASHI Osamu
Department of Ophthalmology, Shiga University of Medical Science
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Yamamoto Y
Osaka City Univ. Osaka Jpn
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HAMADA Masayuki
ULSI Device Development Laboratories NEC Corporation
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Hayashi Osamu
Department Of Ophthalmology Shiga University Of Medical Science
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Hayashi Osamu
International Reagent Corporation
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Hamada M
Ulsi Device Development Laboratories Nec Corporation
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Hamada Masayuki
Department Of Agricultural Chemistry And Faculty Of Agriculture Kinki University
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Hayashi Osamu
Department Of Health And Nutrition Kagawa Nutrition University
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KAWAGUCHI Mamoru
International Reagent Corporation
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YAMAMOTO Yukio
Institute for Chemical Research, Kyoto University
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SAKAI Noriyuki
Department of Agricultural Chemistry, Kinki University
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Kawaguchi M
Hosei Univ. Jpn
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Sakai N
Keio Univ. Yokohama Jpn
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