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Titolo:
Samarium diiodide-promoted sequential coupling-aldol-reduction reactions of ferrocene-substituted enones
Autore:
Jong, SJ; Chen, CT; Fang, JM; Liu, YH; Lee, GH; Wang, Y;
Indirizzi:
Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan Natl Taiwan Univ Taipei Taiwan 106 n Univ, Dept Chem, Taipei 106, Taiwan
Titolo Testata:
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE
fascicolo: 6, volume: 4, anno: 2001,
pagine: 487 - 496
SICI:
1387-1609(200106)4:6<487:SDSCRO>2.0.ZU;2-T
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA,BETA-UNSATURATED KETONES; ELECTROPHILIC REACTIONS; CYCLODIMERIZATION; DIMERIZATION; MOIETIES; CHALCONE;
Keywords:
samarium diiodide; ferrocene; alpha,beta-unsaturated ketones; coupling reaction;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
19
Recensione:
Indirizzi per estratti:
Indirizzo: Fang, JM Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan Natl Taiwan UnivTaipei Taiwan 106 ept Chem, Taipei 106, Taiwan
Citazione:
S.J. Jong et al., "Samarium diiodide-promoted sequential coupling-aldol-reduction reactions of ferrocene-substituted enones", CR AC S IIC, 4(6), 2001, pp. 487-496

Abstract

On treatment with SmI2 in THF, 1 -ferrocenyl-3-phenyl- 2-propen-1-one and its related ferrocene-substituted enones underwent cyclodimerizations to give aldols (2a-g) with 3,4-trans configuration. Further reduction by using increased amounts of SmI2 produced the corresponding diols. The stereoselectivity in this study was comparable with that in the SmI2-promoted cyclodimerization of chalcones, but in contrast to that in the SmI2-promored cyclization-aldol reaction of 1,1'-dicinnamoylferrocenes. The thienyl- and furyl-substituted enones 5a and 5b could be visualized as an extended system of conjugated ketones, so thar the SmI2-mediated coupling reactions occurred preferably by linkages of beta -carbons with thiophene or furan rings, giving compounds 8a,b and 9a,b. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.

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Documento generato il 02/04/20 alle ore 00:21:53