1073147-02-0Relevant academic research and scientific papers
Synthesis of highly functionalized pyrrolidines via a selective iodide-mediated ring expansion of methylenecyclopropyl amides
Scott, Mark E.,Lautens, Mark
supporting information; experimental part, p. 8154 - 8162 (2009/04/04)
(Chemical Equation Presented) This manuscript describes a highly selective iodide-mediated, tandem Mannich/cyclization to afford trans-2,3-disubstituted pyrrolidines from methylenecyclopropyl amides in good to excellent yields and selectivities. The reaction scope has been drastically expanded to include a wide array of aromatic, heteroaromatic and α,β-unsaturated imines, as well as a variety of methylenecyclopropyl amides. Additionally, mechanistic studies were carried out to ascertain the nature of the ring-opening/ring- closing mechanism using deuterated substrates. Results from these studies indicate that the primary mechanism is an SN2/SN2 ring opening/ring closing and that iodine- or iodide-mediated isomerization of the iodo enolate is likely occurring.
