Stereochemistry-59: New insights into the mechanism of the proline-catalyzed asymmetric robinson cyclization; structure of two intermediates. asymmetric dehydration
作者： Claude Agami , Franck Meynier , Catherine Puchot , Jean Guilhem , Claudine Pascard
DOI: 10.1016/S0040-4020(01)91242-6
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摘要: Abstract Two sets of results give information about the mechanism carbonyl activation by (S)-proline during asymmetric syntheses: (i) X-ray structures two ketols produced proline-induced cyclization triketones; (ii) (S)-Proline-catalyzed dehydration (±)-β leading to optically active enones.
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sci-hub.se 参考文章(28)
C. Agami, M. Fadlallah, Stereochimie-LVIII : Condensation du cyanure de trimethylsilyle sur les enones. cyanhydrines α, β-ethyleniques Tetrahedron. ,vol. 39, pp. 777- 779 ,(1983) , 10.1016/S0040-4020(01)91853-8
TAKANORI SONE, KUNIO HIROI, SHUNICHI YAMADA, Stereochemical Studies. XXVIII. Some Aspects of the Asymmetric Synthesis of (R)-(+)-4-Methyl-4-phenyl-2-cyclohexenone via an Enamine Chemical & Pharmaceutical Bulletin. ,vol. 21, pp. 2331- 2335 ,(1973) , 10.1248/CPB.21.2331
Jean Jacques, André Collet, Samuel H. Wilen, Enantiomers, Racemates, and Resolutions ,(1981)
KUNIO HIROI, SHUNICHI YAMADA, Stereochemical studies. XXXVIII. Asymmetric synthesis of the key compounds for the synthesis of optically active diterpenes. Asymmetric synthesis of optically active 1,2,3,4,5,6-7,8,8a-octahydro-8a-methyl-3,8-naphthalenedione derivatives with L-proline derivatives. Chemical & Pharmaceutical Bulletin. ,vol. 23, pp. 1103- 1109 ,(1975) , 10.1248/CPB.23.1103
James A. Marshall, Alan R. Hochstetler, Synthesis of (+-)-geosmin and the other 1,10-dimethyl-9-decalol isomers Journal of Organic Chemistry. ,vol. 33, pp. 2593- 2595 ,(1968) , 10.1021/JO01270A120
Paul Buchschacher, Jean-Marie Cassal, Andor Fürst, Werner Meier, Beitrag zur asymmetrischen Synthese bicyclischer Verbindungen unter Katalyse mit optisch aktiven Aminosäuren. Synthese von (S)-2-Pyrrolidin-propionsäure und (R)-4-Amino-5-phenylvaleriansäure† Helvetica Chimica Acta. ,vol. 60, pp. 2747- 2755 ,(1977) , 10.1002/HLCA.19770600826
James A. Marshall, Wayne I. Fanta, The Synthesis of Bicyclic Ketols from Cyclohexanones The Journal of Organic Chemistry. ,vol. 29, pp. 2501- 2505 ,(1964) , 10.1021/JO01032A004
Zoltan G. Hajos, David R. Parrish, Asymmetric synthesis of bicyclic intermediates of natural product chemistry Journal of Organic Chemistry. ,vol. 39, pp. 1615- 1621 ,(1974) , 10.1021/JO00925A003
Samuel Danishefsky, Paul Cain, Optically specific synthesis of estrone and 19-norsteroids from 2,6-lutidine Journal of the American Chemical Society. ,vol. 98, pp. 4975- 4983 ,(1976) , 10.1021/JA00432A044
H. Molines, C. Wakselman, Annelation fluorante de composes carbonyles par la fluoro-1 vinylmethylcetone Tetrahedron. ,vol. 32, pp. 2099- 2103 ,(1976) , 10.1016/0040-4020(76)85115-0