STRUCTURAL FACTORS AFFECTING THE SELECTIVITIES IN THE PALLADIUM(II) CATALYZED CYCLIZATION OF N-ALKENYL-2-ALKYNAMIDES

Authors
JIANG HF MA SM ZHU GX LU XY
Citation
Hf. Jiang et al., STRUCTURAL FACTORS AFFECTING THE SELECTIVITIES IN THE PALLADIUM(II) CATALYZED CYCLIZATION OF N-ALKENYL-2-ALKYNAMIDES, Tetrahedron, 52(33), 1996, pp. 10945-10954
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
33
Year of publication
1996
Pages
10945 - 10954
Database
ISI
SICI code
0040-4020(1996)52:33<10945:SFATSI>2.0.ZU;2-X
Abstract
Palladium catalyzed cyclization of N-alkenyl 2-alkynamides occurred sm oothly in the presence of CuCl2 and LiCl affording alpha-chloroalkylid ene-gamma-butyrolactams and alpha-chloroalkylidene-delta-valerolactams stereoselectively. The regioselectivity of the intramolecular C-C dou ble bond insertion was influenced by the substituent group on the subs trate. When an alkyl group was introduced into the 1'-position of the alkenyl, an unusual 1,2-induction occurred. For the 3-substituted 2-al kynamides, only cis-beta,gamma-substituted gamma-butyrolactams were re sulted. Copyright (C) 1996 Elsevier Science Ltd