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

Author:

Liu Xigong1,Liu Lei1ORCID,Zhou Likai1,Jia Kuiyong2

Affiliation:

1. School of Chemistry and Chemical Engineering, Shandong University

2. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University

Abstract

AbstractReported 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.

Funder

National Natural Science Foundation of China

China Postdoctoral Science Foundation

Postdoctoral Innovation Project of Shandong Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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