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. 1996 Jun 17;37(25):4309-4312.
doi: 10.1016/0040-4039(96)00832-5.

Synthesis of Higher α-Chlorovinyl and α-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course

David B Berkowitz  1 , Michelle L Pedersen  1 , Wan-Jin Jahng  1
Affiliations

Synthesis of Higher α-Chlorovinyl and α-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course

David B Berkowitz et al. Tetrahedron Lett. .

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).

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

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