Catalytic Regio- and Enantioselective Boracarboxylation of Arylalkenes with CO2 and Diboron

Zhang，Sudong1; Li，Liping1; Li，Dingxi1; Zhou，You Yun1; Tang，Yong1,2

2023

10.1021/jacs.3c12720

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

Catalytic asymmetric carboxylation of readily available alkenes with CO, an abundant and sustainable one-carbon building block, that gives access to value-added α-stereogenic carboxylic acids in an atom- and step-economic manner is highly attractive. However, it has remained a formidable challenge for the synthetic community. Here, the first example of Cu-catalyzed highly regio- and enantioselective boracarboxylation reaction on various arylalkenes with diboron under an atmospheric pressure of CO is described, which afforded a variety of chiral β-boron-functionalized α-aryl carboxylic acids with up to 87% yield and 97% ee under mild conditions. Importantly, α-substituted arylalkenes could also be subject to this protocol with excellent enantiopurities, thereby rendering an efficient approach for the generation of enantioenriched carboxylic acids with an α-chiral all-carbon quaternary center. Moreover, high functional group tolerance, scalable synthesis, and facile access to bioactive compounds, like (−)-scopolamine, (−)-anisodamine, and (−)-tropicamide, further demonstrated the synthetic utility of this strategy.

SCI ; EI

英语

第一

2-s2.0-85184517794

Scopus

1.Shenzhen Grubbs Institute,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
2.State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai,345 Lingling Lu,200032,China

Zhang，Sudong,Li，Liping,Li，Dingxi,et al. Catalytic Regio- and Enantioselective Boracarboxylation of Arylalkenes with CO2 and Diboron[J]. Journal of the American Chemical Society,2023.

Zhang，Sudong,Li，Liping,Li，Dingxi,Zhou，You Yun,&Tang，Yong.(2023).Catalytic Regio- and Enantioselective Boracarboxylation of Arylalkenes with CO2 and Diboron.Journal of the American Chemical Society.

Zhang，Sudong,et al."Catalytic Regio- and Enantioselective Boracarboxylation of Arylalkenes with CO2 and Diboron".Journal of the American Chemical Society (2023).