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Published on: November 9, 2019
Enantioselective Synthesis of Chiral Dihydroisobenzofurans via Tandem Asymmetric Hydrogenation and Selective
Kejia Yang1, Nan Li1, Zhonghao Geng1
1School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China.
Abstract:
We report a practical one-pot protocol for accessing chiral dihydroisobenzofurans via tandem asymmetric hydrogenation and selective 5-exo-dig oxo-cyclization. This method displays high activity (up to 99% yield and S/C = 2000:1) and excellent selectivity (up to 99% ee and exclusive Z selectivity) across a broad substrate scope. Scale-up reactions and further transformations afforded challenging derivatives bearing cis-1,3-stereogenic centers. The operational simplicity and high efficiency arise from the synergistic dual roles of the metal and base.
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