Chemistry Department, Natural Science Complex , State University of New York at Buffalo , Buffalo , New York 14260 , United States.
Org Lett. 2018 Apr 20;20(8):2133-2137. doi: 10.1021/acs.orglett.8b00282. Epub 2018 Mar 28.
A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis- ortho-functionalized arene.
本文报道了一种新型的铜催化的酚和 N-磺酰基亚胺之间的对映选择性氮杂弗里德尔-克拉夫茨反应,该反应以良好到优秀的收率和优异的对映选择性(高达 99%ee)提供了手性仲苄胺。特别是,首次观察到烷基亚胺具有优异的适用范围。产物的合成实用性在首例双食欲素受体拮抗剂的对映选择性合成中得到了证明,该化合物含有一个胺基手性中心,紧邻双邻位官能化芳烃。