Department of Chemistry, Washington State University , Pullman, Washington 99164-4630, United States.
Org Lett. 2014 Mar 21;16(6):1550-3. doi: 10.1021/ol500474a. Epub 2014 Mar 6.
A catalytic asymmetric version of the exo-selective [C+NC+CC] reaction is reported. This multicomponent reaction utilizes a readily prepared achiral glycyl sultam as the "NC" component and commercially available catalyst components. The method can be applied to a variety of aldehydes ("C" component) and activated alkenes ("CC" component) to provide substituted pyrrolidines in good yields and high enantioselectivities. Of particular note is the ability to employ labile enolizable aldehydes (e.g., acetaldehyde and propionaldehyde) in this reaction.
报告了一种外消旋选择性的 [C+NC+CC] 反应的催化不对称版本。该多组分反应利用易于制备的非手性甘氨酰磺酰胺作为“NC”组分和市售的催化剂组分。该方法可应用于各种醛(“C”组分)和活化烯烃(“CC”组分),以高收率和高对映选择性提供取代的吡咯烷。特别值得注意的是,该反应能够使用不稳定的烯醇化醛(如乙醛和丙醛)。