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General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
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Abstract
The reaction of aldehydes with trichloromethide followed by sodium borohydride or sodium phenylseleno(triethyl)borate under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols. The approach is compatible with sensitive aldehydes including enals and enolizable aldehydes. It also offers convenient access to α-monodeuterated carboxylic acids.
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This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids
Joerg H. Schrittwieser, Verena Resch, Silvia Wallner, Wolf-Dieter Lienhart, Johann H. Sattler, Jasmin Resch, Peter Macheroux, and Wolfgang KroutilThe Journal of Organic Chemistry2011 Article ASAPBiocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids
Joerg H. Schrittwieser, Verena Resch, Silvia Wallner, Wolf-Dieter Lienhart, Johann H. Sattler, Jasmin Resch, Peter Macheroux, and Wolfgang KroutilThe Journal of Organic Chemistry2011 Article ASAPA chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C–C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction ...
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History
- Published In Issue September 04, 2008
- Article ASAPAugust 08, 2008
- Received: July 20, 2008
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