@article{5d7544b56b594914a58e3086c6e96349,
title = "Synthesis of higher α-chlorovinyl and α-bromovinyl amino acids: The amino protecting group determines the reaction course",
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).",
author = "Berkowitz, {David B.} and Pedersen, {Michelle L.} and Jahng, {Wan Jin}",
note = "Funding Information: Financiasl upporftr omt heN ationaIln stituteos f Health( CA 62034)is gratefullayc knowledgedM.. L.P. is ther ecipienot f a PatriciaR obertsH arrisF ellowshipfr omt heU .S. Departmenotf Education(P 094B20126). The authortsh ankD r. RichardS hoemake(Ur niversitoy f Nebraskaf)o r technicaals sistancaen dD r. Ron C.erny (NebraskCa enterf or Mass Spectrometrfyo)r high resolutionm asss pectra.T his researchw asf acilitatedb y grantsf or NMR and GC/MS instrumentatiofrno m the NIH (SIG 1-$10-RR06301a)n d the NSF (CHE-9300083)1, r espectively.",
year = "1996",
month = jun,
day = "17",
doi = "10.1016/0040-4039(96)00832-5",
language = "English (US)",
volume = "37",
pages = "4309--4312",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd",
number = "25",
}