Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes.

Marie S T Morin, Sara Aly, Bruce A Arndtsen

Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC H3A 0B8, Canada.

Chemical communications (Cambridge, England) 2013 Jan 30

filter terms:

2-Pyrrolines can be generated by the PhP(2-catechyl) mediated coupling of alkene-tethered imines and acid chlorides. This reaction proceeds via phosphorus-containing 1,3-dipoles, which undergo cycloaddition with alkenes with high stereo- and regioselectivity. The modularity of this reaction can be used to assemble a range of polysubstituted pyrrolines in one pot transformations.

Citation

Marie S T Morin, Sara Aly, Bruce A Arndtsen. Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes. Chemical communications (Cambridge, England). 2013 Jan 30;49(9):883-5