Pd-Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction

Angewandte Chemie
Qiang ChengShu-Li You

Abstract

Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane-anthranil complex which has been confirmed by NMR experiments.

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Citations

Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
Nov 17, 2020·Angewandte Chemie·Yong XiaXiaoming Feng
May 13, 2021·Organic & Biomolecular Chemistry·Ziying ZhangQilin Wang
Jun 5, 2021·Chemical Science·Shengzu DuanPatrick J Walsh
May 30, 2020·The Journal of Organic Chemistry·Yi LiuWenhai Li
May 30, 2020·Chemical Reviews·Vincent PirenneJerome Waser
Dec 6, 2019·The Journal of Organic Chemistry·Xingyu ZhangZhuo Chai
Jul 8, 2020·Organic Letters·Tapas AdakA Stephen K Hashmi
Aug 27, 2019·The Journal of Organic Chemistry·Ryo TanakaShigeki Matsunaga

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