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Home   •   Spotlight  •  rlist2q07j  •  Most Requested Journal Articles 2Q07-Chemistry and Related Science (8)

Most Requested Journal Articles 2Q07-Chemistry and Related Science

Following is one of the journal articles most requested by researchers using CAS electronic products.

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CAS indexed 46 chemical substances from this document. CAS subject entries for this document include: Silanes; Aldehydes, reactions; Arylation; and 11 additional concepts.

CAPLUS COPYRIGHT 2007 ACS on STN

TITLE:	Enantioselective Organocatalysis Using SOMO Activation
AUTHOR(S):	Beeson, Teresa D.; Mastracchio, Anthony; Hong, Jun-Bae; Ashton, Kate; MacMillan, David W. C.
CORPORATE SOURCE:	Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ, 08544, USA
SOURCE:	Science (Washington, DC, United States) (2007), 316(5824), 582-585 CODEN: SCIEAS; ISSN: 0036-8075
PUBLISHER:	American Association for the Advancement of Science
LANGUAGE:	English

ABSTRACT:
The asym. .alpha.-addn. of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in org. 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 addn. 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 MO (SOMO) activation with a highly selective .alpha.-allylation of aldehydes, and we here present preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades.