REGIOSELECTIVITY AND STEREOSELECTIVITY IN REACTIONS OF 2,3-CIS-3-ALKYL-2-VINYLAZIRIDINES AND TRANS-3-ALKYL-2-VINYLAZIRIDINES WITH ORGANOCOPPER REAGENTS - IMPORTANCE OF 2,3-CIS-STEREOCHEMISTRY IN CONTROLLING SELECTIVITY

Authors
AOYAMA H MIMURA N OHNO H ISHII K TODA A TAMAMURA H OTAKA A FUJII N IBUKA T
Citation
H. Aoyama et al., REGIOSELECTIVITY AND STEREOSELECTIVITY IN REACTIONS OF 2,3-CIS-3-ALKYL-2-VINYLAZIRIDINES AND TRANS-3-ALKYL-2-VINYLAZIRIDINES WITH ORGANOCOPPER REAGENTS - IMPORTANCE OF 2,3-CIS-STEREOCHEMISTRY IN CONTROLLING SELECTIVITY, Tetrahedron letters, 38(42), 1997, pp. 7383-7386
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
42
Year of publication
1997
Pages
7383 - 7386
Database
ISI
SICI code
0040-4039(1997)38:42<7383:RASIRO>2.0.ZU;2-P
Abstract
By treatment with organocopper reagents, N-activated 2,3-cis-3-alkyl-2 -vinylaziridines produced exclusively (E)-allyl amines in high yields, presumably via an anti-S(N)2' reaction pathway. On the other hand, un der otherwise identical conditions, N-activated 2,3-trans-3-alkyl-2-vi nylaziridines gave an 85-96:15-4 mixture of (E)- and (Z)-allyl amines. In reactions of certain N-activated 2,3-trans-3-alkyl-2-vinylaziridin es, S(N)2 reaction products were obtained in only 2-3% yield. (C) 1997 Elsevier Science Ltd.