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
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01379