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. 2015 Oct 5;54(41):12134-8.
doi: 10.1002/anie.201505926. Epub 2015 Aug 28.

Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes

Yazhou Lou  1   2 , Peng Cao  1   2 , Tao Jia  1   2 , Yongling Zhang  1   2 , Min Wang  1   2 , Jian Liao  3   4   5
Affiliations

Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes

Yazhou Lou et al. Angew Chem Int Ed Engl. .

Abstract

Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium trifluoroborates into triarylmethanes with highly enantiospecificity was realized.

Keywords: asymmetric catalysis; boron; copper; cross-coupling; synthetic methods.

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