Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

Mahesh P. Paudyal; Mingliang Wang; Juha H. Siitonen; Yimin Hu; Muhammed Yousufuddin; Hong C. Shen; John R. Falck; László Kürti

doi:10.1039/D0OB02122A

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Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles†

Mahesh P. Paudyal,‡^a Mingliang Wang,‡^b Juha H. Siitonen,

^c Yimin Hu,^d Muhammed Yousufuddin,^e Hong C. Shen,*^d John R. Falck

*^a and László Kürti

*^c

Author affiliations

* Corresponding authors

^a Division of Chemistry, Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
E-mail: j.falck@utsouthwestern.edu

^b Department of Natural Products Chemistry, Fudan University, 826 Zhangheng Road, Shanghai 201203, P. R. China

^c Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77030, USA
E-mail: lk18@rice.edu

^d Roche Pharma Research & Early Development, Roche Innovation Center Shanghai, Roche R&D Center (China) Ltd, Building 5, No. 371, Lishizhen Road, Shanghai 201203, P. R. China
E-mail: hong.shen.hs1@roche.com

^e Life and Health Sciences Department, The University of North Texas at Dallas, 7400 University Hills Boulevard, Dallas, TX 75241, USA

Abstract

A mild Rh-catalyzed method for synthesis of cyclic unprotected N–Me and N–H 2,3-aminoethers using an olefin aziridination–aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB02122A
Article type: Communication
Submitted: 20 Oct 2020
Accepted: 17 Dec 2020
First published: 21 Dec 2020

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Org. Biomol. Chem., 2021,19, 557-560

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Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

M. P. Paudyal, M. Wang, J. H. Siitonen, Y. Hu, M. Yousufuddin, H. C. Shen, J. R. Falck and L. Kürti, Org. Biomol. Chem., 2021, 19, 557 DOI: 10.1039/D0OB02122A

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Organic & Biomolecular Chemistry

Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles†

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Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

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