Department of Chemistry, Colorado State University, Fort Collins, 80526, USA.
Angew Chem Int Ed Engl. 2011 Aug 22;50(35):7982-3. doi: 10.1002/anie.201102920. Epub 2011 Jun 30.
N-Heterocyclic carbenes interact with aldehydes to generate the Breslow intermediate, a rendering of the prototypical electrophile into a nucleophile (umpolung). Recent work has indicated that these intermediates may also add to simple, unpolarized alkenes. The use of a chiral precatalyst leads to the generation of the derived adducts with high yields and very high selectivities.
N-杂环卡宾与醛反应生成 Breslow 中间体,将典型的亲电试剂转化为亲核试剂(反转极性)。最近的研究表明,这些中间体也可能与简单的非极化烯烃加成。使用手性前催化剂可以高产率和非常高的选择性得到衍生加成产物。