Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

被引：61

作者：

Anderson, Christopher D. ^{[2
]}

Dudding, Travis ^{[1
]}

Gordillo, Ruth ^{[2
]}

Houk, K. N. ^{[2
]}

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 13期

关键词：

D O I：

10.1021/ol800875k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3-tert-butyldimethylsiloxy butadiene catalyzed by (R,R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.

引用

页码：2749 / 2752

页数：4

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