Wang Bi, Gao Jing-Kun, Sun Shuo, Shen Zhen-Lu, Yang Yun-Fang, Liang Ren-Xiao, Jia Yi-Xia
College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Org Lett. 2024 May 10;26(18):3739-3743. doi: 10.1021/acs.orglett.4c00775. Epub 2024 Apr 28.
An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of -(-bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba)/SPINOL-based phosphoramidite as the chiral catalyst and HCONa as the hydride source, a series of enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The reductive Heck reaction of formal tetrasubstituted alkene bearing β-hydrogens is therefore realized by inhibiting β-H elimination.
开发了一种对映选择性钯催化的-(-溴芳基)吲哚-3-甲酰胺的分子内脱芳构化还原Heck反应。通过使用Pd(dba)/基于SPINOL的亚磷酰胺作为手性催化剂，HCONa作为氢化物源，以中等到良好的产率和优异的对映选择性得到了一系列带有相邻立体中心的对映体富集的螺吲哚啉。因此，通过抑制β-H消除实现了带有β-氢的形式上四取代烯烃的还原Heck反应。
