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Science. 2007 Apr 27;316(5824):582-5. Epub 2007 Mar 29.

Enantioselective organocatalysis using SOMO activation.

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1
Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.

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.

PMID:
17395791
DOI:
10.1126/science. 1142696
[Indexed for MEDLINE]
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