Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

作     者：Lin Tao Qingyang Zhao Xumu Zhang Xiu-Qin Dong Lin Tao;Qingyang Zhao;Xumu Zhang;Xiu-Qin Dong

作者机构：Key Laboratory of Biomedical PolymersEngineering Research Centre of Organosilicon Compounds&MaterialsMinistry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072China Department of Chemistry and Shenzhen Grubbs InstituteSouthern University of Science and TechnologyShenzhen 518055China School of Pharmaceutical Sciences(Shenzhen)Sun Yat-sen UniversityShenzhen 518107China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2020年第31卷第7期

页      面：1859-1862页

核心收录：

学科分类：081702[工学-化学工艺] 08[工学] 0817[工学-化学工程与技术] 

基　　金：the National Natural Science Foundation of China(Nos.21432007,21502145,21602172) Wuhan Morning Light Plan of Youth Science and Technology(No.2017050304010307) the Fundamental Research Funds for and the Central Universities(No.2042018kf0202) Shenzhen Nobel Prize Scientists Laboratory Project(No.C17783101) Science and Technology Innovation Committee of Shenzhen(No.KQTD 20150717103157174) SZDRC Discipline Construction Program The Program of Introducing Talents of Discipline to Universities of China(111 Project) 

主　　题：Chiral 4-substituted chromanes Asymmetric hydrogenation Excellent enantioselectivity Gram-scale synthesis Bisphosphine-thiourea ligand 

摘      要：Rh/ZhaoPhos-catalyzed asymmetric hydroge nation of a series of(E)-2-(chro man-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities(up to 99%yield,98%ee).Moreover,the gram-scale hydrogenation could be performed well in the presence of 0.02 mol%catalyst loading(TON=5000),the hydrogenation product was easily converted to access other important compounds,which demonstrated the synthetic utility of this asymmetric catalytic methodology.