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Zenichi Yoshida (1925-2023)
Zenichi Yoshida (1925-2023)
Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
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May 11, 2023
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Paper | Regular issue | Vol 27, No. 7, 1988, pp.1685-1696
Published online, 1st January, 1970■ Introduction of Alkyl Groups at the α-Positions of Pyrrolidines and Piperidines: Synthesis of (±)-Coniine
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4567
■ Introduction of Alkyl Groups at the α-Positions of Pyrrolidines and Piperidines: Synthesis of (±)-Coniine
Tatsuo Nagasaka,* Hideki Hayashim and Fumiko Hamaguchi
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
The conversion of lactams to α-alkylated cyclic amines is described. Reactions of α-ethoxyurethanes with trimethylsilyl cyanide in the presence of Levis acid afford the corresponding α-cyanourethanes, which, via carbanion, are alkylated to α-alkyl-α-cyanourethanes in moderate to high yields. Syntheses of (±)-coniine and trans-quinolizidine are carried out as model experiments for dealkoxycarbonylation and decyanation of 2-alkyl-1-alkoxycarbonyl-2-cyanopiperidines.
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