Tetrahedron Letters p. 4309 - 4312 (1996)
Update date:2022-09-26
Topics:
Berkowitz, David B.
Pedersen, Michelle L.
Jahng, Wan-Jin
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)-external 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).
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