Catalytic properties of 4,5-bridged proline methano- and ethanologues in the Hajos-Parrish intramolecular aldol reaction  

作　　者：Sofiane Hocine Gilles Berger K.N.Houk Stephen Hanessian 

机构地区：[1]aDepartment of Chemistry,Universitéde Montréal,Station Centre-Ville,C.P.6128,Montreal,QC,H3C 3J7,Canada [2]Microbiology,Bioorganic&Macromolecular Chemistry,Faculty of Pharmacy,UniversitéLibre de Bruxelles,Bd du Triomphe,1050 Brussels,Belgium [3]Department of Chemistry and Biochemistry,University of California,Los Angeles,CA 90095-1569,USA

出　　处：《Organic Chemistry Frontiers》2022年第3期649-659,共11页有机化学前沿（英文）

基　　金：We thank NSERC for financial assistance.We also thank Thierry Maris and Michel Simard from the X-ray diffraction laboratory of the Universitéde Montréal for X-ray analysis。

摘　　要：The catalysis of the Hajos-Parrish reaction by cis-and trans-4,5-ethano-proline was explored experimentally and computationally with DFT(ωB97X-D and MN15)and DLPNO-CCSD(T).Both of the new catalysts are as active as proline or cis-and trans-4,5-methano-proline,with the trans-ethano-proline being as enantioselective as proline.A thorough theoretical analysis of the electronic factors influencing catalysis is reported.

关 键 词：CCSD(T) PROLINE CATALYSIS 

分 类 号：O64[理学—物理化学]