Enantioselective Intramolecular Desymmetric ct-Addition of Cyclohexa- none to Propiolamide Catalyzed by Sodium L-Prolinate
作者机构：College of Chemical EngineeringState Key Laboratory Breeding Base of Green-Chemical Synthesis TechnologyZhejiang University of TechnologyHangzhouZhejiang 310014China Department of ChemistryZhejiang UniversityHangzhouZhejiang 310027China Shanghai Key Laboratory for Molecular Engineering of Chlral DrugsShanghai Jiao Tong University800 Dongchuan RoadShanghai 200240China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2019年第37卷第1期
页 面：63-70页
核心收录：
基 金：the National Natural Science Foundation of China (Nos.21522207,21702184,and 21772175,YXJ and RXL) the Chinese "Thousand Youth Talents Plan"(XH),and the Chinese "Fundamental Research Funds for the Central Universities" (XH)
主 题：enantioselective scaffold group
摘 要：Summary of main observation and conclusion An enantioselective desymmetric nucleophilic α-addition of cyclohexanone to propiolamide has been developed through a 6-exo-dig cyclization *** employing simple and readily available L-proline sodium salt as a bifunctional catalyst,a series of chiral 6,6-bicyclic bridged products bearing morphan scaffold have been isolated in good yields and excellent *** functional theory (DFT)calculations elucidated the origins of the enantioselectivity and regioselectivity of this transformation.A salt bridge that links the amide carbonyl group with proline carboxylate in the transition state was proven to be the driving force for the induction of excellent enantioselectivity.
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