184044-75-5Relevant academic research and scientific papers
Stereoselective synthesis of enantiopure 6-fluoromethyl furo[3,4-c]- isoxazolidines
Bandiera, Paola,Bravo, Pierfrancesco,Bruche, Luca,Zanda, Matteo,Arnone, Alberto
, p. 2665 - 2677 (1998)
The title compounds 7a-c are prepared through a totally regio- and stereo-selective intramolecular 1,3-dipolar cycloaddition of nitrones; a chiral and optically pure sulfinyl function acts as a removable primary source of stereocontrol.
A CYCLOADDITIVE ROUTE TO ENANTIOMERICALLY PURE 6-FLUOROMETHYL FUROISOXAZOLIDININES
Bandiera, Paola,Bravo, Pierfrancesco,Bruche, Luca,Zanda, Matteo,Arnone, Alberto
, p. 773 - 776 (2007/10/03)
A synthetic sequence to the title compounds is described, starting from the chiral and optically pure β-keto sulphoxide 1.The protocol involves Pummerer rearrangement of β-allyloxy sulphoxides 3 to the aldehydes 5, which are transformed in situ into the transient nitrones 6: these provide directly the bicyclic compounds 7, through a fully regio- and diastereo-selective intramolecular 1,3-dipolar cycloaddition.
