Studies on the Oxazaborolidine-catalyzed Enantioselective Reduction of 3-Morpholin-4-yl-1-phenyl-1-propanone with Density Functional Theory

作     者：FANJian-Fen LUYun-Xiang WANGQiu-Xia WULi-Fen SUNYun-Peng 

作者机构：DepartmentofChemistrySuzhouUniversitySuzhou215006China 

出 版 物：《Chinese Journal of Structural Chemistry》 (结构化学（英文）)

年 卷 期：2005年第24卷第4期

页      面：413-418页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070304[理学-物理化学(含∶化学物理)] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：Project supported by the Research Foundation of Suzhou University (Q3109306) 

主　　题：B3LYP/6-31G* 3-morpholin-4-yl-1-phenyl-1-propanone enantioselective reduction 

摘      要：Density functional theory (DFT) has been applied to study the enantioselective reduction of 3-morpholin-4-yl-1-phenyl-1-propanone with borane catalyzed by (S)-4-benzyl-5,5- diphenyl-1,3,2-oxazaborolidine at the B3LYP/6-31G* level. All molecular species involved in the four reaction steps have been fully optimized and the structural parameters are provided, and the micro process of reaction was also investigated. The catalyst-alkoxyborane adduct formed in step III exhibits a B-O-B-N tetra-atomic ring. Reaction coordination calculations show that BH3 can react with 3-morpholin-4-yl-1-phenyl-1-propanone spontaneously, resulting in the need of 2 mol BH3 in the reaction.