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
收藏
页码：14578 / 14581
页数：4
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