Enantioselective Transfer Hydrogenation of Oxocarbenium Ions Enables Asymmetric Access to α-Substituted 1,3-Dihydroisobenzofurans

Likai Zhou; Kuiyong Jia; Xigong Liu; Lei Liu

doi:10.1055/a-1643-8526

Synthesis, Table of Contents

Synthesis 2022; 54(02): 421-428
DOI: 10.1055/a-1643-8526

paper

Enantioselective Transfer Hydrogenation of Oxocarbenium Ions Enables Asymmetric Access to α-Substituted 1,3-Dihydroisobenzofurans

Likai Zhou

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China

,

Kuiyong Jia

^bDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan 250012, P. R. of China

,

Xigong Liu∗

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China

,

Lei Liu ∗

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China

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Abstract

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Abstract

Reported here is an efficient enantioselective transfer hydrogenation of cyclic oxocarbenium ions generated in situ through collapse of the corresponding acetal substrates. The asymmetric approach provides straightforward access to a variety of chiral α-aryl substituted 1,3-dihydroisobenzofurans in high yields with excellent enantioselectivities. α-Alkynyl substituted 1,3-dihydroisobenzofurans were also proved to be suitable substrates. In addition, when the reaction was performed at gram scale, the desired product was obtained in good yields with excellent enantioselectivity.

Key words

enantioselectivity - transfer hydrogenation - oxocarbenium ions - α-substituted 1,3-dihydroisobenzofurans - asymmetric catalysis

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References

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