Chirality transfer in the ene-reactions of 3-{2-(2S)-[2-(substituted)vinyl]pyrrolidin-1-yl}-2-(substituted)acrolein derivatives

Authors
Noguchi, M Matsushita, R Takamura, S Uchida, T Kakehi, A Shiro, M Yamamoto, H
Citation
M. Noguchi et al., Chirality transfer in the ene-reactions of 3-{2-(2S)-[2-(substituted)vinyl]pyrrolidin-1-yl}-2-(substituted)acrolein derivatives, TETRAHEDR L, 41(44), 2000, pp. 8489-8493
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
44
Year of publication
2000
Pages
8489 - 8493
Database
ISI
SICI code
0040-4039(20001028)41:44<8489:CTITEO>2.0.ZU;2-R
Abstract
Ene-reactions of 3-{2-(2S)-[2-(substituted)vinyl]pyrrolidin-1-yl}-2-(substi tuted)acrolein derivatives 5, 8, 13, and 16 have been described. Carbonyl-e ne reaction of 5 and 16 and imine-ene reaction of 8 proceeded in a highly s elective manner to lead to azepine derivatives 6 and 17, and 9, respectivel y. The chirality of the starting acroleins was transferred almost perfectly to the azepine-ring through the ene reactions. (C) 2000 Elsevier Science L td. All rights reserved.