Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions

被引：174

作者：

Burns, Noah Z. ^{[1
]}

Witten, Michael R. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 37期

关键词：

2-DIAZO-3,6-DIKETOESTER-DERIVED CARBONYL YLIDES; 1,3-DIPOLAR CYCLOADDITION; ALKENE CYCLOADDITIONS; TUMOR PROMOTERS; SELECTIVITY; DITERPENE; ADDITIONS; ACCESS; ROUTE;

D O I：

10.1021/ja206997e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.

引用

页码：14578 / 14581

页数：4

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