State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Org Lett. 2015 Feb 6;17(3):528-31. doi: 10.1021/ol503537w. Epub 2015 Jan 21.
A simple catalyst system of Rh(I)/sulfur-olefin with exceptional catalytic performance has been developed for the highly enantioselective arylation of cyclic N-sulfonyl aryl alkyl ketimines with arylboroxines/arylboronic acids. Optically active α-arylalkyl-substituted benzosultams and benzosulfamidates which are generally difficult to obtain were easily prepared with excellent stereocontrol (up to 99.9% ee). The synthetic utility of the approach was demonstrated by the facile construction of NMDA antagonist FR115427 and benzoxazinone derivatives. This protocol offers new opportunities for the efficient synthesis of diverse chiral α-tertiary amines.
已开发出一种简单的 Rh(I)/硫-烯烃催化剂体系，用于高度对映选择性地芳基化环状 N-磺酰基芳基烷基酮亚胺与芳基硼酸酯/硼酸。通常难以获得的光学活性α-芳基烷基取代的苯并噻唑烷和苯并磺酰胺很容易通过出色的立体控制（高达 99.9%ee）来制备。该方法的合成实用性通过 NMDA 拮抗剂 FR115427 和苯并恶嗪酮衍生物的简便构建得到了证明。该方案为高效合成各种手性α-叔胺提供了新的机会。
