TY - JOUR
T1 - Enantioselective organo-SOMO cycloadditions
T2 - A catalytic approach to complex pyrrolidines from olefins and aldehydes
AU - Jui, Nathan T.
AU - Garber, Jeffrey A.O.
AU - Finelli, Fernanda Gadini
AU - MacMillan, David W.C.
PY - 2012/7/18
Y1 - 2012/7/18
N2 - 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 styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
AB - 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 styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
UR - http://www.scopus.com/inward/record.url?scp=84863956269&partnerID=8YFLogxK
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U2 - 10.1021/ja305076b
DO - 10.1021/ja305076b
M3 - Article
C2 - 22764834
AN - SCOPUS:84863956269
SN - 0002-7863
VL - 134
SP - 11400
EP - 11403
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 28
ER -