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Titolo:
Studies on the synthesis of 2,6-disubstituted dihydropyrans: Intervention of oxonia-Cope rearrangements in the Lewis acid mediated cyclodehydrative reactions of aldehydes and beta-hydroxyallylsilanes
Autore:
Roush, WR; Dilley, GJ;
Indirizzi:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan Ann ArborMI USA 48109 , Dept Chem, Ann Arbor, MI 48109 USA
Titolo Testata:
SYNLETT
, , anno: 2001,
pagine: 955 - 959
SICI:
0936-5214(2001):<955:SOTSO2>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
SAKURAI ISMS REACTION; STEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; OKADAIC ACID; CYCLIZATIONS; TETRAHYDROPYRANS; EFFICIENT; ETHERS; ACETYLATION; SPIROKETALS;
Keywords:
addition reactions; intramolecular allylations; sigmatropic rearrangement; allylsilanes; dihydropyrans;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Roush, WR Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ MichiganAnn Arbor MI USA 48109 m, Ann Arbor, MI 48109 USA
Citazione:
W.R. Roush e G.J. Dilley, "Studies on the synthesis of 2,6-disubstituted dihydropyrans: Intervention of oxonia-Cope rearrangements in the Lewis acid mediated cyclodehydrative reactions of aldehydes and beta-hydroxyallylsilanes", SYNLETT, 2001, pp. 955-959

Abstract

The dehydrative coupling reactions of anti-beta -hydroxyallylsilanes 5 andaldehydes provide 2,6-cis-dihydropyrans 27 by pathways involving oxonium ions that cyclize via boat-like transition state 21, with the intervention of oxonia-Cope rearrangements (21 --> 29).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/04/20 alle ore 07:24:14