Lewis base activation of lewis acids: Development of a Lewis base catalyzed selenolactonization

被引:106
作者
Denmark, Scott E. [1 ]
Collins, William R. [1 ]
机构
[1] Univ Illinois, Roger Adams Lab, Dept Chem, Urbana, IL 61801 USA
关键词
D O I
10.1021/ol701617d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reaction are seen. Preliminary mechanistic investigations have revealed the resting state of the catalyst as well as the significance of a weak Bronsted acid promoter.
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页码:3801 / 3804
页数:4
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