Rowland Gerald B, Rowland Emily B, Liang Yuxue, Perman Jason A, Antilla Jon C
Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE205A, Tampa, FL 33620, USA.
Org Lett. 2007 Jul 5;9(14):2609-11. doi: 10.1021/ol0703579. Epub 2007 Jun 5.
The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported. A total of 15 examples with product yield ranging from 89% to 99% and enantioselectivities from 90% to 97% are presented. A chiral phosphoric acid catalyst derived from a hindered binol derivative was employed most effectively in the reaction. Attractive features of the reaction include desirable catalyst loadings, good reactivity, generality of substrates, and easily removable groups from both nitrogen atoms.
报道了N-苄基吲哚对N-酰基亚胺的高度对映选择性有机催化加成反应。给出了总共15个例子，产物产率为89%至99%，对映选择性为90%至97%。一种由受阻联萘酚衍生物衍生的手性磷酸催化剂在该反应中得到了最有效的应用。该反应的吸引人之处包括理想的催化剂用量、良好的反应活性、底物的通用性以及两个氮原子上易于去除的基团。
