Enantioselective organo-SOMO cycloadditions: A catalytic approach to complex pyrrolidines from olefins and aldehydes
NT Jui, JAO Garber, FG Finelli…
文献索引：Jui, Nathan T.; Garber, Jeffrey A.O.; Finelli, Fernanda Gadini; MacMillan, David W.C. Journal of the American Chemical Society, 2012 , vol. 134, # 28 p. 11400 - 11403
A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3+ 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including ...
