SYNTHESIS OF HIGHER ALPHA-CHLOROVINYL AND ALPHA-BROMOVINYL AMINO-ACIDS - THE AMINO PROTECTING GROUP DETERMINES THE REACTION COURSE

Authors
BERKOWITZ DB PEDERSEN ML JAHNG WJ
Citation
Db. Berkowitz et al., SYNTHESIS OF HIGHER ALPHA-CHLOROVINYL AND ALPHA-BROMOVINYL AMINO-ACIDS - THE AMINO PROTECTING GROUP DETERMINES THE REACTION COURSE, Tetrahedron letters, 37(25), 1996, pp. 4309-4312
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
25
Year of publication
1996
Pages
4309 - 4312
Database
ISI
SICI code
0040-4039(1996)37:25<4309:SOHAAA>2.0.ZU;2-Q
Abstract
N-Trifluoroacetyl alpha-vinyl amino esters are smoothly converted to t he corresponding alpha-chlorovinyl or alpha-bromovinyl amino esters th rough the agency of phenyselenyl chloride or phenylselenyl bromide, re spectively, followed by oxidation and pyrolysis. Exclusively the (E)-e xternal halovinyl isomer and the internal halovinyl isomer am observed . The amino protecting group is a critical determinant of the reaction course (alkene addition vs. 5-exo-trig-like cyclization). Copyright ( C) 1996 Elsevier Science Ltd.