Chiral Cyclopropenyl Ketones: Reactive and Selective Diels鈥揂lder Dienophiles
详细信息 查看全文
- 作者：Laural A. Fisher ; Natalee J. Smith ; Joseph M. Fox
- 刊名：The Journal of Organic Chemistry
- 出版年：2013
- 出版时间：April 5, 2013
- 年：2013
- 卷：78
- 期：7
- 页码：3342-3348
- 全文大小：303K
- 年卷期：v.78,no.7(April 5, 2013)
- ISSN：1520-6904
文摘
The synthesis and Diels鈥揂lder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels鈥揂lder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.