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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
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- 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