Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InP-Pd(0)-promoted metalation

Authors
Takemoto, Y Anzai, M Yanada, R Fujii, N Ohno, H Ibuka, T
Citation
Y. Takemoto et al., Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InP-Pd(0)-promoted metalation, TETRAHEDR L, 42(9), 2001, pp. 1725-1728
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1725 - 1728
Database
ISI
SICI code
0040-4039(20010226)42:9<1725:SSON1A>2.0.ZU;2-Z
Abstract
Treatment of optically active 3-alkyl-2-vinylaziridines 1, 8 and 9 and ally lic acetates 10 and 11 with InI in the presence of Pd(PPh3)(4) gives rise t o chiral allylindiums bearing an amino group at the delta -position, which react with several aldehydes in highly regio- and stereoselective manner to afford the syn,syn-2-vinyl-1,3-amino alcohols 2a, 5a-7a and 12a-14a posses sing three contiguous chiral centers in good yields. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.