A radical cyclization route to pyrrolidines based on conjugate addition toelectron deficient phenylselenenylalkenes

Authors
Berlin, S Engman, L
Citation
S. Berlin et L. Engman, A radical cyclization route to pyrrolidines based on conjugate addition toelectron deficient phenylselenenylalkenes, TETRAHEDR L, 41(19), 2000, pp. 3701-3704
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3701 - 3704
Database
ISI
SICI code
0040-4039(20000506)41:19<3701:ARCRTP>2.0.ZU;2-I
Abstract
alpha-Phenylselenenyl-alpha,beta-unsaturated esters, amides, ketones, nitri les and sulfones were prepared by zinc chloride promoted chloroselenation/d ehydrochlorination of the corresponding alpha,beta-unsaturated compounds. A fter Michael addition of allyl or propargylamine and triethylborane initiat ed reductive radical cyclization in the presence of tris(trimethylsilyl)sil ane, pyrrolidine and dihydropyrrole derivatives, respectively, were obtaine d. (C) 2000 Elsevier Science Ltd. All rights reserved.