Chemistry, Department of
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Document Type
Article
Date of this Version
6-17-1996
Citation
Tetrahedron Lett. 1996 June 17; 37(25): 4309–4312. doi:10.1016/0040-4039(96)00832-5.
Abstract
N-Trifluoroacetyl α-vinyl amino esters are smoothly converted to the corresponding α-chlorovinyl or α-bromovinyl amino esters through the agency of phenyselenyl chloride or phenylselenyl bromide, respectively, followed by oxidation and pyrolysis. Exclusively the (E)-extemal halovinyl isomer and the internal halovinyl isomer are observed. The amino protecting group is a critical determinant of the reaction course (alkene addition vs. 5-exo-trig-like cyclization).
Included in
Analytical Chemistry Commons, Medicinal-Pharmaceutical Chemistry Commons, Other Chemistry Commons
Comments
Copyright (c) 1996 Elsevier Inc. Used by permission.