Enantioselective organocatalysis using SOMO activation

Teresa D. Beeson, Anthony Mastracchio, Jun Bae Hong, Kate Ashton, David W.C. MacMillan

Research output: Contribution to journalArticle

482 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)582-585
Number of pages4
JournalScience
Volume316
Issue number5824
DOIs
StatePublished - Apr 27 2007

All Science Journal Classification (ASJC) codes

  • General

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    Beeson, T. D., Mastracchio, A., Hong, J. B., Ashton, K., & MacMillan, D. W. C. (2007). Enantioselective organocatalysis using SOMO activation. Science, 316(5824), 582-585. https://doi.org/10.1126/science. 1142696