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Organocatalytic SOMO reactions of copper(I)-acetylide and alkylindium compounds with aldehydes

Pavol Tisovský, Mária Mečiarová, and Radovan Šebesta

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15, Bratislava, Slovakia

 

E-mail: radovan.sebesta@fns.uniba.sk

Abstract: The derivatisation of aldehydes in their α-position is an important facet of organic synthesis. Organocatalytic radical reactions afford α-functionalised aldehydes via a SOMO activation pathway. New organo-SOMO reactions of aldehydes with copper(I)-acetylide and alkylindium reagents are detailed. These reactions proceed well under the catalysis of chiral imidazolidinones. The corresponding functionalised aldehydes were obtained with acceptable yields, but with only low enantiomeric ratios.

Keywords: organocatalysis – SOMO activation – acetylide – alkylindium

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-014-0564-4

 

Chemical Papers 68 (8) 1113–1120 (2014)

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