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A convenient method for synthesis of optically active 2,3-methanopipecolic acid

✍ Scribed by Yoshihiro Matsumura; Mayumi Inoue; Yasuharu Nakamura; Idi Ludwig Talib; Toshihide Maki; Osamu Onomura

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
138 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

2,3-Didehydro-1,2-bis(methoxycarbonyl)-6-methoxypiperidine (4), prepared from l-lysine by using electrochemical oxidation, was cyclopropanated with high diastereoselectivity (96.6% de), and the cyclopropanated product was transformed to optically active 2,3-methanopipecolic acid (1). In this transformation, the 6-methoxy group of 4 was found to be an eective chiral auxiliary.

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