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Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers

Rh-Catalysis: A regio- and enantioselective atom-economic catalytic addition of 1,3-diketones to allenes is reported furnishing tertiary and quaternary all-carbon stereocenters under mild reaction conditions. The reaction shows a broad functional-group tolerance and numerous variations on both reaction partners highlight its synthetic utility.

Abstract

An unprecedented highly regio- and enantioselective rhodium-catalyzed addition of 1,3-diketones to terminal and 1,1-disubstituted allenes furnishing asymmetric tertiary and quaternary all-carbon centers is reported. By applying a RhI/phosphoramidite/TFA catalytic system under mild conditions, the desired chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with perfect regioselectivity and in high enantioselectivity. The reaction shows a broad functional-group tolerance on both reaction partners highlighting its synthetic potential.

 

 

T. M. Beck, B. Breit, Angew. Chem. 2017, 129, 1929-1933; (link) Angew. Chem. Int. Ed. 2017, 56, 1903-1907 (link).

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