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. 2021 Mar 22;60(13):7093-7097.
doi: 10.1002/anie.202016001. Epub 2021 Feb 17.

Catalytic Enantioselective Aminopalladation-Heck Cascade

Yu-Ping He  1 , Jian Cao  1   2 , Hua Wu  1 , Qian Wang  1 , Jieping Zhu  1
Affiliations

Catalytic Enantioselective Aminopalladation-Heck Cascade

Yu-Ping He et al. Angew Chem Int Ed Engl. .

Abstract

Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2-alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc)2 , a chiral bidentate pyrox ligand and O2 as terminal oxidant affords the structurally diverse indole-cyclopentene conjugates bearing two stereocenters in a highly diastereo- and enantio-selective manner. One of the products is converted to a heavily functionalized tetracyclic indolinone derivative.

Keywords: asymmetric synthesis; domino reactions; homogeneous catalysis; nucleopalladation; oxidative Heck reactions.

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References

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