Jump to main content
Jump to site search


Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones

Author affiliations

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

Back to tab navigation

Supplementary files

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, Advance Article
  •   Request permissions

    Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones

    P. Huang and H. Geng, Green Chem., 2018, Advance Article , DOI: 10.1039/C7GC03534A

Search articles by author

Spotlight

Advertisements