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

Authors
Matsumura, Y Inoue, M Nakamura, Y Talib, IL Maki, T Onomura, O
Citation
Y. Matsumura et al., A convenient method for synthesis of optically active 2,3-methanopipecolicacid, TETRAHEDR L, 41(23), 2000, pp. 4619-4622
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
23
Year of publication
2000
Pages
4619 - 4622
Database
ISI
SICI code
0040-4039(20000612)41:23<4619:ACMFSO>2.0.ZU;2-V
Abstract
2,3-Didehydro-1,2-bis(methoxycarbonyl)-6-methoxypiperidine (4), prepared fr om L-lysine by using electrochemical oxidation, was cyclopropanated with hi gh diastereoselectivity (96.6% de), and the cyclopropanated product was tra nsformed to optically active 2,3-methanopipecolic acid (1). In this transfo rmation, the 6-methoxy group of 4 was found to be an effective chiral auxil iary. (C) 2000 Elsevier Science Ltd. All rights reserved.