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.

引用

页码：1925 / 1932

页数：8

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