Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins
A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.
Jui, Nathan T.,Lee, Esther C. Y.,MacMillan, David W. C.
supporting information; experimental part
p. 10015 - 10017
(2010/10/03)
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