Enantioselective α-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway

…, J Kong, BN Laforteza, DWC MacMillan

Index: Conrad, Jay C.; Kong, Jongrock; Laforteza, Brian N.; MacMillan, David W. C. Journal of the American Chemical Society, 2009 , vol. 131, # 33 p. 11640 - 11641

Full Text: HTML

Citation Number: 148

Abstract

The intramolecular α-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π- electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent electron-rich aromatics and ...