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Titolo:
Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates:controlled syntheses of trisubstituted olefins from 1-alkynes
Autore:
Gerard, J; Hevesi, L;
Indirizzi:
Fac Univ Notre Dame Paix, Dept Chim, B-5000 Namur, Belgium Fac Univ Notre Dame Paix Namur Belgium B-5000 him, B-5000 Namur, Belgium
Titolo Testata:
TETRAHEDRON
fascicolo: 44, volume: 57, anno: 2001,
pagine: 9109 - 9121
SICI:
0040-4020(20011029)57:44<9109:CEIRO1>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
CROSS-COUPLING REACTIONS; SPECIFICALLY PROTECTED 1,3-DIKETONES; BETA-UNSATURATED KETONES; STEREOSELECTIVE SYNTHESIS; VINYLIC TELLURIDES; GRIGNARD-REAGENTS; ORGANOTELLURIUM COMPOUNDS; STEREOSPECIFIC SYNTHESIS; REDUCTIVE ALKYLATION; ORGANIC TELLURIDES;
Keywords:
olefin synthesis; alkynyltrialkyl borate; rearrangement; vinyl boranes; vinyl sulphides; vinyl selenides; vinyl tellurides;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
61
Recensione:
Indirizzi per estratti:
Indirizzo: Hevesi, L Fac Univ Notre Dame Paix, Dept Chim, 61 Rue Bruxelles, B-5000 Namur, Belgium Fac Univ Notre Dame Paix 61 Rue Bruxelles Namur Belgium B-5000
Citazione:
J. Gerard e L. Hevesi, "Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates:controlled syntheses of trisubstituted olefins from 1-alkynes", TETRAHEDRON, 57(44), 2001, pp. 9109-9121

Abstract

The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces beta -chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation-protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed coupling with Grignard reagents. Sincethe last two steps occur with retention of the stereochemistry, the overall sequence represents a highly regio- and stereoselective olefin synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/12/20 alle ore 12:45:20