Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• diphenyl phosphoryl azide (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

Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis

• Jingran Tao,
• Li-Mei Jin and
• X. Peter Zhang

Beilstein J. Org. Chem. 2014, 10, 1282–1289, doi:10.3762/bjoc.10.129

• (2,2,2-trichloroethyl)phosphoryl azide (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; phosphoryl azide; 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 phosphoryl azide, 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