Synthesis of higher α-chlorovinyl and α-bromovinyl amino acids: The amino protecting group determines the reaction course

David B. Berkowitz, Michelle L. Pedersen, Wan Jin Jahng

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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)-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).

Original languageEnglish (US)
Pages (from-to)4309-4312
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number25
DOIs
StatePublished - Jun 17 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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