Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines

Yuse Kuriyama; Yusuke Sasano; Yoshiharu Iwabuchi

doi:10.3389/fchem.2023.1251299

Azetidine synthesis by La(OTf)₃-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines

Front Chem. 2023 Sep 19:11:1251299. doi: 10.3389/fchem.2023.1251299. eCollection 2023.

Authors

Yuse Kuriyama¹, Yusuke Sasano¹, Yoshiharu Iwabuchi¹

Affiliation

¹ Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.

Abstract

Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf)₃-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines to afford azetidines. This reaction proceeded in high yields even in the presence of acid-sensitive and Lewis basic functional groups.

Keywords: Lewis acid; azetidine; catalytic reaction; cyclization; epoxide; regioselectivity; synthetic methods.

Grants and funding

This research was partially supported by JSPS KAKENHI Grant Nos. 22H02739 and 21H05210 (Digitalization-driven Trans-formative Organic Synthesis (Digi-TOS)), and by Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP22ama121040.