Enantioselective organocatalysis using SOMO activation |
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| Authors: | Beeson Teresa D Mastracchio Anthony Hong Jun-Bae Ashton Kate Macmillan David W C |
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| Institution: | Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, USA. |
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| Abstract: | The asymmetric alpha-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 alpha-allylation of aldehydes, and we here present preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades. |
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