Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich-hydroamination reactions.

Alexandre Jean (1) , Jérôme Blanchet (1) , Jacques Rouden (1) , Jacques Maddaluno (2) , Michaël de Paolis (2)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A one-pot sequence of organocatalytic transformations delivers heteroarylmethylene-substituted pyrrolidines with high stereo- and enantioselectivity. A Mannich coupling of N-heteroarylalkyne aldehydes with aldimine and an original metal-free hydroamination of the resulting adducts are the key transformations of the process delivering highly functionalized molecules with high potential for synthetic applications.

Domaines: Chimie organique

Alexandre Jean, Jérôme Blanchet, Jacques Rouden, Jacques Maddaluno, Michaël de Paolis. Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich-hydroamination reactions.. Chemical Communications, 2013, 49 (16), pp.1651-1653. ⟨10.1039/c2cc38954a⟩. ⟨hal-00871123⟩