62847-66-9Relevant academic research and scientific papers
Asymmetric Synthesis of 2H-Azirines with a Tetrasubstituted Stereocenter by Enantioselective Ring Contraction of Isoxazoles
Okamoto, Kazuhiro,Nanya, Atsushi,Eguchi, Akira,Ohe, Kouichi
supporting information, p. 1039 - 1043 (2018/01/26)
Highly strained 2H-azirines with a tetrasubstituted stereocenter were synthesized by the enantioselective isomerization of isoxazoles with a chiral diene–rhodium catalyst system. The effect of ligands and the coordination behavior support the proposed cat
Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines
Rostovskii, Nikolai V.,Agafonova, Anastasiya V.,Smetanin, Ilia A.,Novikov, Mikhail S.,Khlebnikov, Alexander F.,Ruvinskaya, Julia O.,Starova, Galina L.
, p. 4478 - 4488 (2017/09/26)
A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.
