Chiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C-H Activation/Cycloaddition Reactions

被引：17

作者：

Gonzalez, Jose Manuel ^{[1
,2
]}

Vidal, Xandro ^{[1
,2
]}

Ortuno, Manuel Angel ^{[1
,2
]}

Mascarenas, Jose Luis ^{[1
,2
]}

Gulias, Moises ^{[1
,2
]}

机构：

[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 47期

关键词：

KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; EFFICIENT APPROACH; ACTIVATION; FUNCTIONALIZATION; ANNULATION; IODINATION; RH; BENZYLAMINES; C(SP(2))-H;

D O I：

10.1021/jacs.2c09479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the first examples of the use of a new class of ligands (NOBINAc) for performing asymmetric C-H activations using palladium catalysts. These ligands combine the axial chirality of binaphthyl scaffolds with the bifunctional and bidentate coordination properties of mono-N-protected amino acids (MPAAs), which are well-known to favor Pd-promoted C-H activations via concerted metalation-deprotonation mechanisms. We demonstrate that our new ligands enable substantially higher enantioselectivities than MPAAs in the assembly of 2-benzazepines through formal (5 + 2) cycloadditions between homobenzyltriflamides or o-methylbenzyltriflamides and allenes.

引用

收藏

页码：21437 / 21442

页数：6

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