Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects

被引：96

作者：

Wang, Yidong ^{[1
]}

Zhang, Peichao ^{[1
]}

Liu, Yuan ^{[1
]}

Xia, Fei ^{[1
]}

Zhang, Junliang ^{[1
,2
]}

机构：

[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 10期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; CYCLOADDITION REACTIONS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; CASCADE REACTIONS; ALLENYL AMIDES; INDOLES; LIGANDS; ALKENES; TETRAHYDROCARBAZOLES;

D O I：

10.1039/c5sc01827g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective [2+2] versus a [4+2]-cycloaddition of 3-styrylindoles to N-allenamides catalyzed by identical gold(I)/chiral phosphoramidite complexes is presented, which provides facile access to synthetically valuable, optically active substituted cyclobutanes and tetrahydrocarbazoles. The cycloaddition mode unexpectedly depends on the electronic nature of the N-substituent 3-styrylindoles, the origin of which could be well rationalized using DFT calculations and experimental results. To the best of our knowledge, the present work represents the first example of such an impressive substituent effect in tuning the reaction mode with high chemo-, regio- and enantioselectivity in asymmetric gold catalysis.

引用

页码：5564 / 5570

页数：7

共 88 条

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