期刊
TETRAHEDRON
卷 68, 期 2, 页码 481-487出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.11.019
关键词
Ab initio methods; Cascade/domino reaction; Density functional theory methods; Diastereoselectivity; Reaction mechanism
Theoretical calculations were employed to investigate the diastereoselectivity of the alpha,alpha-diphenylprolinol trimethylsilyl ether-catalyzed two-component cascade reactions between (i) pentane-1,5-dial and nitrostyrene, and (ii) pentane-1,5-dial and an alpha,beta-unsaturated carbonyl compound. In both cases, the enol mechanism was able to account for the enantioselectivity of not only the major diastereomer formed, but also that of the minor diastereomers. Insights gained from our mechanistic investigations have enabled us to develop a scheme for the synthesis of cyclohexanes with six stereogenic centers, via two-component one-pot catalytic domino reactions. (C) 2011 Elsevier Ltd. All rights reserved.
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