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Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of β-Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbon Centers

Changkun Li and Bernhard Breit*

*Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau, Germany, Email: bernhard.breitchemie.uni-freiburg.de

C. Li, B. Breit, J. Am. Chem. Soc., 2014, 136, 650-652.

DOI: 10.1021/ja411397g (free Supporting Information)


Abstract

A Rh(I)/DPPF system enables a chemo- and regioselective intermolecular decarboxylative addition of β-ketoacids to terminal allenes, in which tertiary and quaternary carbon centers were formed with exclusively branched selectivity under mild conditions. Preliminary mechanism studies support that the decarboxylation follows the carbon-carbon bond formation and the reaction occurs in an outer-sphere mechanism.

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Key Words

carbonyl compounds


ID: J48-Y2014