Lewis acid-promoted reaction of β,γ-unsaturated α,α-dimethoxy esters with silyl nucleophiles

被引：3
作者：
Sugimura, Hideyuki [1 ]
Miyazaki, Hiiro [1 ]
Makita, Yui [1 ]
机构：
[1] Aoyama Gakuin Univ, Dept Chem & Biol Sci, Chuo Ku, Sagamihara, Kanagawa 2522558, Japan
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 34期
关键词：
Mukaiyama aldol reaction; Hosomi-Sakurai allylation; beta; gamma-Unsaturated alpha-keto esters; gamma-Substituted alpha; beta-unsaturated alpha-methoxy esters; DIELS-ALDER REACTIONS; ALPHA-KETO ESTERS; MUKAIYAMA-MICHAEL REACTIONS; FRIEDEL-CRAFTS ALKYLATION; ENOLATE CLAISEN REARRANGEMENT; C-H BONDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; STEREOCONTROLLED SYNTHESIS;
D O I：
10.1016/j.tetlet.2012.06.078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Lewis acid-promoted reaction of beta,gamma-unsaturated alpha,alpha-dimethoxy esters, which are easily prepared by the acetalization of beta,gamma-unsaturated alpha-keto esters, with silyl nucleophiles is presented. By employing trimethylsilyl enolate and allyltrimethylsilane as nucleophiles, the BF3-promoted reactions of a series of beta,gamma-unsaturated alpha,alpha-dimethoxy esters bearing aromatic and aliphatic substituents proceeded at the gamma-position in an SN2' manner to furnish gamma-substituted alpha,beta-unsaturated alpha-methoxy esters in good yields with high regioselectivity. In contrast, the reaction using trimethylsilyl cyanide predominantly occurred at the alpha-position, and the reaction of silyl hydride resulted in a mixture of alpha- and gamma-regioisomers in favor of the gamma-substitution products. (C) 2012 Elsevier Ltd. All rights reserved.
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页码：4584 / 4587
页数：4
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