Beilstein J. Org. Chem.2019,15, 2577–2589, doi:10.3762/bjoc.15.251
diphenyl phosphorylazide (DPPA), trimethylsilyl azide (TMSA) and tetrabutylammonium azide (TBAA) are suitable for the reaction.
Continuous flow C-3 mesyl shikimate azidation using either DPPA or TMSA. The use of either DPPA or TMSA as the azidating agent for mesyl shikimate 4 was investigated in a
PDF
Graphical Abstract
Scheme 1:
Handling of azide chemistry in Tamiflu synthesis by Hayashi and co-workers [14].
Beilstein J. Org. Chem.2014,10, 1282–1289, doi:10.3762/bjoc.10.129
(2,2,2-trichloroethyl)phosphorylazide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to
; cobalt complex; metalloradical catalysis; organophosphorus; phosphorylazide; Introduction
Aziridines, the smallest three-membered nitrogen-containing heterocycles, are highly valuable heterocyclic compounds that are widely used in organic synthesis and pharmaceuticals [1][2]. As a result, tremendous
asymmetric version of olefin aziridination with phosphorylazide, both the yields and enantioselectivities were moderate even using 10 mol % catalyst loading. It would be desirable if a more effective Co(II)-based metalloradical system could be developed for asymmetric aziridination of alkenes with
PDF
Graphical Abstract
Scheme 1:
[Co(TPP)]-catalyzed olefin aziridination with DPPA.