Journal
GREEN CHEMISTRY
Volume 20, Issue 3, Pages 593-599Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7gc03534a
Keywords
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Funding
- National Key RAMP
- D Program of China [2017YFA0207302]
- National Natural Science Foundation of China [21332007, 21472153]
- Program for Changjiang Scholars and Innovative Research Team in the University of Ministry of Education, China
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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.
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