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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.