Issue 18, 2016
From the journal:

RSC Advances

Diastereoselective synthesis of 3,3-dimethylazetidines via an intramolecular iodine-mediated cyclization reaction†

Hai-Shan Jin,‡a   Rui Sun,‡a   Wei Zhoua  and  Li-Ming Zhao*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, Jiangsu, China
E-mail: lmzhao@jsnu.edu.cn

Abstract

A number of bioactive molecules possess a 3,3-dimethylazetidine moiety. An iodine-mediated intramolecular cyclization reaction of γ-prenylated amines has been developed to provide a convenient route to 3,3-dimethylazetidines in a highly diastereoselective manner. The presented approach not only offers a new strategy for the synthesis of the bioactively important 3,3-dimethylazetidines but also provides an opportunity to extend the application of γ-prenylated amine synthons in organic synthesis.

Graphical abstract: Diastereoselective synthesis of 3,3-dimethylazetidines via an intramolecular iodine-mediated cyclization reaction

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Article information

DOI
https://doi.org/10.1039/C5RA21872A
Article type
Paper
Submitted
20 Oct 2015
Accepted
25 Jan 2016
First published
28 Jan 2016

RSC Adv., 2016,6, 15035-15038

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Diastereoselective synthesis of 3,3-dimethylazetidines via an intramolecular iodine-mediated cyclization reaction

H. Jin, R. Sun, W. Zhou and L. Zhao, RSC Adv., 2016, 6, 15035 DOI: 10.1039/C5RA21872A

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