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Titolo:
Highly stereoselective intramolecular Michael addition using alpha-sulfinyl vinyllithium as an unprecedented Michael donor
Autore:
Maezaki, N; Yuyama, S; Sawamoto, H; Suzuki, T; Izumi, M; Tanaka, T;
Indirizzi:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 eut Sci, Suita, Osaka 5650871, Japan
Titolo Testata:
ORGANIC LETTERS
fascicolo: 1, volume: 3, anno: 2001,
pagine: 29 - 31
SICI:
1523-7060(20010111)3:1<29:HSIMAU>2.0.ZU;2-4
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA,BETA-UNSATURATED SULFOXIDES; ORGANOSULFUR COMPOUNDS; PHOSPHORYL SULFOXIDES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; PARA-TOLYL; ESTERS; DECONJUGATION; CARBANIONS; RESOLUTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
27
Recensione:
Indirizzi per estratti:
Indirizzo: Maezaki, N Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka 5650871, Japan Osaka Univ 1-6 Yamadaoka Suita Osaka Japan 5650871 50871, Japan
Citazione:
N. Maezaki et al., "Highly stereoselective intramolecular Michael addition using alpha-sulfinyl vinyllithium as an unprecedented Michael donor", ORG LETT, 3(1), 2001, pp. 29-31

Abstract

[GRAPHICS]The first example of an asymmetric intramolecular Michael addition reaction using cr lithiated vinylic sulfoxide as a Michael donor is reported. Michael addition of the alpha -lithiated vinylic sulfoxide to (Z)-enoates proceeds with high diastereoselectivity to give the adducts having a stereogeniccenter with (R)-configuration at the beta -position of the ester in the cyclopentene ring formation. The selectivity was reversed in the six-memberedring formation. On the other hand, the corresponding (E)-enoates provided Michael adducts with poor diastereoselectivity.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/01/20 alle ore 15:47:14