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

页码：3636 / 3639

页数：4

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