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Titolo:
External chiral ligand-induced enantioselective versions of the [2,3]-Wittig sigmatropic rearrangement
Autore:
Tomooka, K; Komine, N; Nakai, T;
Indirizzi:
Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol Tokyo Japan 1528552 , Meguro Ku, Tokyo 1528552, Japan
Titolo Testata:
CHIRALITY
fascicolo: 5-6, volume: 12, anno: 2000,
pagine: 505 - 509
SICI:
0899-0042(2000)12:5-6<505:ECLEVO>2.0.ZU;2-9
Fonte:
ISI
Lingua:
ENG
Soggetto:
BENZYL PRENYL ETHERS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; LITHIATION; ENOLATE; COMPLEX; SYSTEM;
Keywords:
asymmetric synthesis; asymmetric catalysis; bis(oxazolines); butyllithiums; enantioselectivity; propargylic alcohols; sparteine;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
23
Recensione:
Indirizzi per estratti:
Indirizzo: Nakai, T Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol Tokyo Japan 1528552 Ku, Tokyo 1528552, Japan
Citazione:
K. Tomooka et al., "External chiral ligand-induced enantioselective versions of the [2,3]-Wittig sigmatropic rearrangement", CHIRALITY, 12(5-6), 2000, pp. 505-509

Abstract

The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis(oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the "asymmetric catalytic version" of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/01/20 alle ore 18:39:58