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Ni-Catalyzed Chemoselective Alcoholysis of N-Acyloxazolidinones

Abstract

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupies an important position in modern organic synthesis, the catalytic cleavage of the (chiral)auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displayed good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

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Publication details

The article was received on 23 Nov 2017, accepted on 27 Dec 2017 and first published on 05 Jan 2018


Article type: Communication
DOI: 10.1039/C7GC03534A
Citation: Green Chem., 2018, Accepted Manuscript
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    Ni-Catalyzed Chemoselective Alcoholysis of N-Acyloxazolidinones

    P. Huang and H. Geng, Green Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7GC03534A

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