Highly stereoselective metal-mediated domino aldol reactions of propiophenone enolates with heteroaromatic, aliphatic, and unsaturated aldehydes

被引：0
|
作者：
Cinar, M. Emin [1 ]
Schmittel, Michael [1 ]
机构：
[1] Univ Siegen, Dept Chemie Biol, Dept Biol Chem, Adolf Reichwein Str 2, D-57068 Siegen, Germany
来源：
MONATSHEFTE FUR CHEMIE | 2016年 / 147卷 / 11期
关键词：
Tetrahydropyran; Enolates; Diastereo-selective reaction; Aldol reactions; Natural products; Density functional theory; EFFECTIVE CORE POTENTIALS; NATURAL-PRODUCT SYNTHESIS; MOLECULAR CALCULATIONS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; DENSITY; THERMOCHEMISTRY; MECHANISM; ELEMENTS; MICHAEL;
D O I：
10.1007/s00706-016-1841-4
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The one-pot reaction of propiophenone with heteroaromatic, aliphatic, and unsaturated aldehydes in the presence of metal halides furnishes racemic tetrahydro-2H-pyran-2,4-diols in a highly diastereo-selective manner. The mechanism for the stereoselective product formation as well as the surprising formation of a side product was explained on the basis of DFT computations.
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页码：1925 / 1932
页数：8
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