Divergent synthesis of oxazolidines and morpholines via PhI(OAc)2-mediated difunctionalization of alkenes

Shuang Yang; Yuhang Chen; Zidan Yuan; Feiyu Bu; Cheng Jiang; Zhenhua Ding

doi:10.1039/D0OB01987A

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Divergent synthesis of oxazolidines and morpholines via PhI(OAc)₂-mediated difunctionalization of alkenes†

Shuang Yang,^a Yuhang Chen,^a Zidan Yuan,^a Feiyu Bu,^a Cheng Jiang^a and Zhenhua Ding

*^a

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* Corresponding authors

^a Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China
E-mail: zhding@cpu.edu.cn

Abstract

Herein we describe the PhI(OAc)₂-mediated 1,1- and 1,2-difunctionalization of alkenes with N-tosyl amino alcohols to form oxazolidine and morpholine derivatives. This transformation was realized under mild reaction conditions and allows application to various substrates furnishing the multi-substituted oxazolidines and morpholines with yields up to 98%. A deuterium-labeling experiment was carried out and the result indicated that a phenyl group migration occurred to generate oxazolidine products.

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

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Article information

DOI: https://doi.org/10.1039/D0OB01987A
Article type: Paper
Submitted: 29 Sep 2020
Accepted: 23 Nov 2020
First published: 24 Nov 2020

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Org. Biomol. Chem., 2020,18, 9873-9882

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Divergent synthesis of oxazolidines and morpholines via PhI(OAc)₂-mediated difunctionalization of alkenes

S. Yang, Y. Chen, Z. Yuan, F. Bu, C. Jiang and Z. Ding, Org. Biomol. Chem., 2020, 18, 9873 DOI: 10.1039/D0OB01987A

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Organic & Biomolecular Chemistry