Issue 3, 2018

Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones

Abstract

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a 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 displays 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.

Graphical abstract: Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones

Supplementary files

Article information

Article type
Communication
Submitted
23 noy 2017
Accepted
27 dek 2017
First published
05 yan 2018

Green Chem., 2018,20, 593-599

Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones

P. Huang and H. Geng, Green Chem., 2018, 20, 593 DOI: 10.1039/C7GC03534A

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