锌促进的烷基碘化物、α,β-不饱和酯（或腈）和酰化剂三种组分的区域选择性和序列选择性一锅法连接反应。

Zn-promoted regioselective and sequence-selective one-pot joining reaction of three components: alkyl iodides, alpha,beta-unsaturated esters (or nitriles), and acylating agents.

作者信息

Yamamoto Yoshimasa, Nakano Seiji, Maekawa Hirofumi, Nishiguchi Ikuzo

机构信息

Department of Chemistry, Nagaoka University of Technology, 1603-1 Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan.

出版信息

Org Lett. 2004 Mar 4;6(5):799-802. doi: 10.1021/ol036506e.

DOI:10.1021/ol036506e

PMID:14986978

Abstract

One-pot treatment of alkyl iodides, alpha,beta-unsaturated esters (or nitriles), and acylating agents such as nitriles or acid anhydrides in the presence of Zn metal at room temperature in the same reaction system brought about a regioselective and sequence-selective three-component joining reaction involving first C-alkylation at the beta-position and second C-acylation at the alpha-position of alpha,beta-unsaturated esters (or nitriles) to afford the corresponding alpha,alpha-dialkylketoesters (or alpha,alpha-dialkylketonitriles) in moderate to good yields. [reaction: see text]

摘要

在室温下，将烷基碘、α,β-不饱和酯（或腈）以及诸如腈或酸酐等酰化剂在相同反应体系中于锌金属存在下进行一锅法处理，可引发区域选择性和顺序选择性的三组分连接反应，该反应首先在α,β-不饱和酯（或腈）的β位进行C-烷基化，然后在α位进行C-酰化，从而以中等至良好的产率得到相应的α,α-二烷基酮酯（或α,α-二烷基酮腈）。[反应：见正文]