Origins of Aryl Substituent Effects on the Stereoselectivities of Additions of Silyl Enol Ethers to a Chiral Oxazolinium Ion

被引：5

作者：

Krenske, Elizabeth H. ^{[1
,2
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Australian Res Council Ctr Excellence Free Rad Ch, Melbourne, Vic, Australia

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 24期

基金：

澳大利亚研究理事会;

关键词：

4+3 CYCLOADDITIONS; NONCOVALENT INTERACTIONS; 2-METHOXY OXAZOLIDINES; DENSITY FUNCTIONALS; THERMOCHEMISTRY; FORMYLATION; ENERGIES; CATIONS;

D O I：

10.1021/ol202911v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Density functional theory calculations are reported that reveal the role of aromatic interactions in the additions of aryl-substituted silyl enol ethers to a chiral oxazolinium ion. Aryl-substituted silyl enol ethers give the opposite diastereomer of the adduct than do aliphatic silyl, enol ethers, due to a combination of attractive cation-pi and CH-pi interactions, reduced steric repulsion, and lower torsional strain in the more "crowded" transition state.

引用

页码：6572 / 6575

页数：4

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