Synthesis 2022; 54(02): 421-428
Enantioselective Transfer Hydrogenation of Oxocarbenium Ions Enables Asymmetric Access to α-Substituted 1,3-Dihydroisobenzofurans
Likai Zhou
a
School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
Kuiyong Jia
b
Department 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∗
a
School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
a
School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
› Author Affiliations This work was financially supported by the Postdoctoral Innovation Project of Shandong Province (No. 202001003), the National Science Foundation of China (No. 21801093), and China Postdoctoral Science Foundation (No. 2019M662321).
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
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-1643-8526.
Supporting Information
Publication History
Received: 22 July 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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