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Titolo:
A highly stereoselective synthesis of (E)-alpha-bromoacrylates
Autore:
Tago, K; Kogen, H;
Indirizzi:
Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan Sankyo Co Ltd Tokyo Japan 1408710 bs, Shinagawa Ku, Tokyo 1408710, Japan
Titolo Testata:
TETRAHEDRON
fascicolo: 45, volume: 56, anno: 2000,
pagine: 8825 - 8831
SICI:
0040-4020(20001103)56:45<8825:AHSSO(>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
Z-UNSATURATED ESTERS; CROSS-COUPLING REACTIONS; TRISUBSTITUTED ALKENES; SELECTIVE SYNTHESIS; HELICOBACTER-PYLORI; WITTIG OLEFINATION; STEREOCHEMISTRY; PLAUNOTOL; REAGENTS; KETONES;
Keywords:
olefination; synthetic methods; stereocontrol; phosphonic acid and derivatives;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
47
Recensione:
Indirizzi per estratti:
Indirizzo: Kogen, H Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, 1-2-58 Hiromachi, Tokyo 1408710, Japan Sankyo Co Ltd 1-2-58 Hiromachi Tokyo Japan 1408710 408710, Japan
Citazione:
K. Tago e H. Kogen, "A highly stereoselective synthesis of (E)-alpha-bromoacrylates", TETRAHEDRON, 56(45), 2000, pp. 8825-8831

Abstract

Novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (5a), was designed and prepared in order to efficiently synthesize (E)-alpha -bromoacrylates 7, from which widely useful precursors for various C-C bond formations were prepared. Horner-Wadsworth-Emmons (HWE) reaction of various aldehydes with 5a in the presence of t-BuOK and 18-C-6 gave corresponding (E)-alpha -bromoacrylate derivatives with high stereoselectivity and excellent yield. Using the product (E)-a-bromoacrylate 7s as a key intermediate, we succeeded in developing the most effective route of plaunotol synthesis via Suzuki cross-coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 15:08:59