MeO-CBS不对称催化还原苯乙酮的量子化学计算  

Quantum calculating study of asymmetric reduction of 1-phenyl-ethanone using MeO-CBS as catalyst

作　　者：宋华付[1] 许家喜[1] 卢永军[1] 金春华 陈云华 

机构地区：[1]北京大学化学与分子工程学院,北京100871 [2]海正药业集团,浙江台州318000

出　　处：《计算机与应用化学》2008年第6期707-710,共4页Computers and Applied Chemistry

摘　　要：在RHF/3-21G水平和基组上得到四氢-1-甲氧基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]吡唑硼啉(MeO-CBS)催化还原苯乙酮反应过程中,各主要中间体和过渡态的优化结构参数和热化学数据,在此基础上预测反应产物的e.e.%值。在相同水平和基组上与四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]吡唑硼啉(Me-CBS)的相关计算结果相比较,可以看出:两种催化剂条件下,主要中间体及过渡态的主要结构参数相似,遵循类似的催化机理;四氢-1-甲氧基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]吡唑硼啉在反应条件下具有更高的对映选择性。optimized structure parameters and relevant thermochemistry data in the chiral reduction process of 1-phenyl-ethanone with 1-methoxy-3,3-diphenyl-tetrahydro-pyrrolo[ 1,2-c]-[ 1,3,2] oxazaborole （MeO-CBS） as catalyst were obtained under RHF/3-21G level. Product e. e. % value was predicted on the basis of these calculated data. The calculating results between the Me-CBS and MeO- CBS as independently catalysts were compared under the same calculating level. It could be concluded that there exits similar catalyzing mechanism to the two catalysts mainly due to the similar intermediates and reaction complexes. Meanwhile, MeO-CBS led to high chiral value of product under the given reaction conditions.

关 键 词：CBS催化剂 苯乙酮 不对称催化还原 量子化学 

分 类 号：O621.36[理学—有机化学] O641.121[理学—化学]