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  • Title: Enantioselective organocatalysis using SOMO activation.
    Author: Beeson TD, Mastracchio A, Hong JB, Ashton K, Macmillan DW.
    Journal: Science; 2007 Apr 27; 316(5824):582-5. PubMed ID: 17395791.
    Abstract:
    The asymmetric α-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that well-established chiral amine catalysis, which activates aldehydes toward electrophile addition by enamine formation, could be expanded to this important reaction class by applying a single-electron oxidant to create a transient radical species from the enamine. We demonstrated the concept of singly occupied molecular orbital (SOMO) activation with a highly selective α-allylation of aldehydes, and we here present preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades.
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