Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction.

Author(s) Zhang, Z.M.; Xu, B.; Wu, L.; Wu, Y.; Qian, Y.; Zhou, L.; Liu, Y.; Zhang, J.
Journal Angew Chem Int Ed Engl
Date Published 2019 Oct 07
Abstract

A highly enantioselective dicarbofunctionalization of unactivated alkenes was implemented by a Pd-catalyzed asymmetric tandem Heck/Suzuki coupling reaction. This reaction represents the first example of a highly enantioselective intramolecular cyclization/cross-coupling of olefin-tethered aryl halides with alkyl-, alkenyl- or arylboronic acids, and provides rapid access to a number of chiral compounds, such as dihydrobenzofurans, indolines, chromanes, and indanes bearing a quaternary stereocenter, in good yields with excellent enantioselectivities. The practicality of this reaction was validated in the modification of biologically complex molecules such as peptides, piperitol, CB2 receptor agonists, etc. Moreover, the synthesis of two enantiomers can be easily realized by simple change in the order of the steps in the coupling sequence.

DOI 10.1002/anie.201907840
ISSN 1521-3773
Citation Zhang Z-, Xu B, Wu L, Wu Y, Qian Y, Zhou L, et al. Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction. Angew Chem Int Ed Engl. 2019;58(41):14653-14659.