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J Am Chem Soc. 2018 Aug 22;140(33):10619-10626. doi: 10.1021/jacs.8b06900. Epub 2018 Aug 9.

Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation.

Author information

1
Department of Chemistry , Georgia State University , 100 Piedmont Avenue SE , Atlanta , Georgia 30303 , United States.

Abstract

We herein report a gram-scale, enantioselective synthesis of Tamiflu, in which the key trans-diamino moiety has been efficiently installed via an iron-catalyzed stereoselective olefin diazidation. This significantly improved, iron-catalyzed method is uniquely effective for highly functionalized yet electronically deactivated substrates that have been previously problematic. Preliminary catalyst structure-reactivity-stereoselectivity relationship studies revealed that both the iron catalyst and the complex substrate cooperatively modulate the stereoselectivity for diazidation. Safety assessment using both differential scanning calorimetry (DSC) and the drop weight test (DWT) has also demonstrated the feasibility of carrying out this iron-catalyzed olefin diazidation for large-scale Tamiflu synthesis.

PMID:
30040881
PMCID:
PMC6108189
[Available on 2019-08-22]
DOI:
10.1021/jacs.8b06900

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