Divergent methods produce cis and trans-2,3-disubstituted pyrrolidines from chiral imines, indicating improved synthetic pathways.
Divergent access to cis and trans-2,3-disubstituted pyrrolidines from platform diastereoenriched homoallylic amines is described. Based on the allylmetalation of chiral imines, using an allylmetal containing a protected hydroxyethyl chain, homoallylic amines can be achieved in a highly diastereoselective manner by suitably adapting the reaction conditions and the chiral auxiliary to the C-substituent of the imine. Subsequent specific activation of either the hydroxyethyl or the vinylic chain promotes the C-N bond-forming cyclization, affording cis or trans pyrrolidines, which can be valued as precursors of polycyclic skeletons.
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Gharbi et al. (2026) studied this question.
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