One-Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols

被引：37

作者：

Dai, Qipu ^{[1
]}

Arman, Hadi ^{[1
]}

Zhao, John Cong-Gui ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 05期

关键词：

cyclohexanol; domino reactions; Henry reaction; Michael addition; organocatalysis; TRICYCLIC CARBON FRAMEWORKS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; MICHAEL ADDITION; CONTIGUOUS STEREOCENTERS; CASCADE REACTIONS; CATALYST; ALDOL; DIASTEREOSELECTIVITY;

D O I：

10.1002/chem.201203104

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereoselective (d.r. >99:1) and enantioselective (ee value up to 96?%) synthesis of trisubstituted cyclohexanols was achieved by using a one-pot sequential organocatalysis that involved a quinidine thiourea-catalyzed tandem HenryMichael reaction between nitromethane and 7-oxo-hept-5-en-1-als followed by a tetramethyl guanidine (TMG)-catalyzed tandem retro-HenryHenry reaction on the reaction products of the tandem HenryMichael reaction. Through a mechanistic study, it has also been demonstrated that similar results may also be achieved with this one-pot sequential organocatalysis by using the racemic Henry product as the substrate.

引用

页码：1666 / 1671

页数：6

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