Organocatalytic 1,4-Addition of Azadienes with 3‑Homoacyl Coumarins toward Highly Enantioenriched Benzofuran Coumarin Skeletons

Organocatalytic 1,4-Addition of Azadienes with 3‑Homoacyl Coumarins toward Highly Enantioenriched Benzofuran Coumarin Skeletons

A highly enantioselective 1,4-addition reaction of azadiene with 3-homoacyl coumarin has been accomplished by low amounts of bifunctional cinchona alkaloid catalysis under mild conditions. Varieties of benzofuran coumarin skeletons were obtained in moderate to high yields (up to 99%) with excellent...

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Veröffentlicht in:Journal of organic chemistry 2020-10, Vol.85 (19), p.12175-12186
Hauptverfasser: Yan, Juzhang, Li, Xiaoping, Chen, Yuzhen, Li, Ying, Chen, Weiwen, Zhan, Ruoting, Huang, Huicai
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container_end_page 12186
container_issue 19
container_start_page 12175
container_title Journal of organic chemistry
container_volume 85
creator Yan, Juzhang
Li, Xiaoping
Chen, Yuzhen
Li, Ying
Chen, Weiwen
Zhan, Ruoting
Huang, Huicai
description A highly enantioselective 1,4-addition reaction of azadiene with 3-homoacyl coumarin has been accomplished by low amounts of bifunctional cinchona alkaloid catalysis under mild conditions. Varieties of benzofuran coumarin skeletons were obtained in moderate to high yields (up to 99%) with excellent enantioselectivities (up to 99% ee) and complete diastereoselectivity.
doi_str_mv 10.1021/acs.joc.0c01379
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title Organocatalytic 1,4-Addition of Azadienes with 3‑Homoacyl Coumarins toward Highly Enantioenriched Benzofuran Coumarin Skeletons
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