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Letter

Catalytic Generation of Activated Carboxylates from Enals: A Product-Determining Role for the Base

Supporting Info

Stephanie S. Sohn and Jeffrey W. Bode*

Department of Chemistry and Biochemistry, University of CaliforniaSanta Barbara, Santa Barbara, California 93101

Org. Lett., 2005, 7 (18), pp 3873–3876

DOI: 10.1021/ol051269w

Publication Date (Web): August 10, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, bode@chem.ucsb.edu

Abstract

N-Heterocycle carbenes generated in situ from imidazolium or triazolium salts and bases react with enals, leading to the catalytic generation of homoenolates. The fate of these intermediates is determined by the catalytic base: strong bases such as ^tBuOK lead to carbon−carbon bond formation, while weaker bases allow protonation of the homoenolate and subsequent generation of activated carboxylates. This discovery, along with the design of a new triazolium precatalyst, enables the catalytic, atom-economical redox esterification of enals.

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Published In Issue September 01, 2005
Received May 30, 2005

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Letter

Catalytic Generation of Activated Carboxylates from Enals: A Product-Determining Role for the Base

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Catalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of β-Hydroxyesters from Epoxyaldehydes

N-Heterocyclic Carbene-Catalyzed Generation of Homoenolates: γ-Butyrolactones by Direct Annulations of Enals and Aldehydes

Catalytic Synthesis of γ-Lactams via Direct Annulations of Enals and N-Sulfonylimines

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