Chiral diamines.: Part 3:: Effect of ligand structure on the enantioselective deprotonation of N-Boc-pyrrolidine with i-PrLi:: a computational comparison of (-)-sparteine and (S,S)-1,2-bis(N,N-dimethylamino)cyclohexane

被引：25

作者：

Wiberg, KB ^{[1
]}

Bailey, WF

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Univ Connecticut, Dept Chem, Storrs, CT 06279 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 49期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)01353-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deprotonation N-Boc-pyrrolidine by i-PrLi-(S,S)-1,2-bis(N,N-dimethylamino)cyclohexane has been studied at the HF/3-21G and B3P86/6-31G* theoretical levels. The two lowest energy complexes of the N-Boc-pyrrolidine-i-PrLi-diamine ligand, as well as the transition states leading to proton transfer, were found to be similar in both geometry and energy in accord with experimental findings. The results are compared to those for the analogous but enantioselective (-)-sparteine-mediated deprotonation. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：9365 / 9368

页数：4

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