411239-45-7Relevant academic research and scientific papers
Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins
Jui, Nathan T.,Lee, Esther C. Y.,MacMillan, David W. C.
supporting information; experimental part, p. 10015 - 10017 (2010/10/03)
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.
