酯酰亚胺（和二酯）的硅氢化类似狄克曼环化反应。

Silylative Dieckmann-like cyclizations of ester-imides (and diesters).

作者信息

Hoye Thomas R, Dvornikovs Vadims, Sizova Elena

机构信息

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

出版信息

Org Lett. 2006 Nov 9;8(23):5191-4. doi: 10.1021/ol061988q.

DOI:10.1021/ol061988q

PMID:17078675

Abstract

[Structure: see text] Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

摘要

[结构：见正文] 三氟甲磺酸三烷基硅酯促使酯酰亚胺（如2）环化生成加合物（如4a）。捕获原位生成的亲核烯酮缩醛（参见5a）是该转化的关键环节。报道了一系列适用于这种操作简单的反应的底物。在许多情况下，非对映选择性水平非常高。从光谱观察结果推断出机理要点。