Asymmetric Synthesis of Highly Functionalized Tetrahydropyrans via a One-Pot Organocatalytic Michael/Henry/Ketalization Sequence

被引：39
|
作者：
Hahn, Robert [1 ]
Raabe, Gerhard [1 ]
Enders, Dieter [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 14期
基金：
欧洲研究理事会;
关键词：
DOMINO MICHAEL/ALDOL REACTIONS; STEREOSELECTIVE-SYNTHESIS; CINCHONA ALKALOIDS; CONTIGUOUS STEREOCENTERS; CASCADE REACTIONS; ALDOL REACTION; HENRY REACTION; CONSTRUCTION; CATALYSIS; TANDEM;
D O I：
10.1021/ol501236a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diastereo- and enantioselective Michael/Henry/ketalization sequence to functionalized tetrahydropyrans is described. The multicomponent cascade reaction uses acetylacetone or beta-keto esters, beta-nitrostyrenes, and alkynyl aldehydes as substrates affording tetrahydropyrans with five contiguous stereocenters. Employing a bifunctional quinine-based squaramide organocatalyst, the title compounds are obtained in moderate to good yields (27-80%), excellent enantiomeric excesses (93-99% ee), and high diastereomeric ratios (dr > 20:1) after one crystallization.
引用
收藏
页码：3636 / 3639
页数：4
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