苯酚导向的醛亚胺和酮亚胺的对映选择性烯丙基化反应。

Phenol-directed enantioselective allylation of aldimines and ketimines.

作者信息

Rabbat Philippe M A, Valdez S Corey, Leighton James L

机构信息

Department of Chemistry, Columbia University, New York, New York 10027, USA.

出版信息

Org Lett. 2006 Dec 21;8(26):6119-21. doi: 10.1021/ol062589y.

DOI:10.1021/ol062589y

PMID:17165944

Abstract

[Structure: see text] Phenols are effective directing and activating groups for our allylchlorosilane reagents, allowing the highly enantioselective allylation of a range of 2-aminophenol-derived aldimines. When the phenol is incorporated into the substrate ketimines may be allylated highly enantioselectively, leading to the experimentally simple synthesis of a range of tertiary carbinamine structures.

摘要

[结构：见正文] 对于我们的烯丙基氯硅烷试剂而言，酚是有效的导向和活化基团，能使一系列2-氨基酚衍生的醛亚胺实现高度对映选择性烯丙基化反应。当酚基引入到底物中时，酮亚胺也能实现高度对映选择性烯丙基化反应，从而通过实验简便地合成一系列叔碳胺结构。