Organic Chemistry Portal



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:

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

DOI: 10.1021/ja411397g (free Supporting Information)


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.

see article for more examples

Key Words

carbonyl compounds

ID: J48-Y2014