Suppr超能文献

[反应名称]:一锅法非对映选择性和对映选择性合成哌啶的[环加成反应名称]。

Domino imino-aldol-aza-Michael reaction: one-pot diastereo- and enantioselective synthesis of piperidines.

机构信息

Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.

出版信息

J Org Chem. 2010 Nov 5;75(21):7061-72. doi: 10.1021/jo101680f.

Abstract

Addition of α-arylmethylidene- or α-alkylidene-β-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.

摘要

通过亚胺醇醛途径将α-芳基甲基-或α-亚烷基-β-酮酯烯醇盐加成到 N-活化的亚胺,然后以级联方式进行分子内氮杂迈克尔反应,开发了一种高度非对映选择性的取代哌啶合成方法。从手性亚砜亚胺合成了对映纯哌啶。通过机理和计算研究对产物的形成和观察到的立体选择性进行了合理化。

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验