Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the -Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides

Article abstract of DOI:10.1021/jo00032a016

A sequence of reactions including <3.3>-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated γ-lactams from allylic alcohols.No δ-lactam was formed as a byproduct.The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity.Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.