通过硝酮1,3-偶极环化加成反应制备功能化氮杂双环烷氨基酸

Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition.

作者信息

Manzoni Leonardo, Arosio Daniela, Belvisi Laura, Bracci Antonio, Colombo Matteo, Invernizzi Donatella, Scolastico Carlo

机构信息

C.N.R.-Istituto di Scienze e Tecnologie Molecolari, and Centro Interdisciplinare Studi bio-molecolari e applicazioni Industriali, Via Venezian 21, I-20133, Milano, Italy.

出版信息

J Org Chem. 2005 May 13;70(10):4124-32. doi: 10.1021/jo0500683.

DOI:10.1021/jo0500683

PMID:15876105

Abstract

[reaction: see text] An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

摘要

[反应：见正文] 已设计出一种高效且操作简便的方法来合成官能化氮杂氧杂双环[X.3.0]烷氨基酸。关键步骤是在5-烯丙基-或5-高烯丙基脯氨酸上进行分子内硝酮环加成反应，该反应具有完全的区域选择性和立体选择性。