Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compoundin THF-DMF: a novel synthesis of 1,2-disubstituted (E)-vinyl bromides

Authors
Hoshi, M Shirakawa, K
Citation
M. Hoshi et K. Shirakawa, Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compoundin THF-DMF: a novel synthesis of 1,2-disubstituted (E)-vinyl bromides, TETRAHEDR L, 41(15), 2000, pp. 2595-2598
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
15
Year of publication
2000
Pages
2595 - 2598
Database
ISI
SICI code
0040-4039(20000408)41:15<2595:RO[WNC>2.0.ZU;2-Z
Abstract
DMF-induced reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with an N-hal ogeno compound results in 1,2-migration of an alkyl group from the dialkylb oryl group to the alpha-carbon atom without elimination of the bromine atom , followed by beta-elimination to provide 1,2-disubstituted (E)-vinyl bromi des stereoselectively in good yields. (C) 2000 Elsevier Science Ltd. All ri ghts reserved.