Construction of Cyclopropa[c]coumarins via cascade Michael-alkylation process of 3-cyanocoumarin with 2-bromomalonate

A convenient and efficient method for the synthesis of highly functionalized cyclopropa[c]coumarin derivatives in good to excellent yields via cascade Michael-alkylation process of 3-substituted coumarins and 2-bromomalonate was developed. Preliminary results indicated that using a chiral PTC strate...

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Bibliographic Details
Published in:Tetrahedron 2020-01, Vol.76 (5), p.130852, Article 130852
Main Authors: Sun, Jun-Chao, Li, Jun-Lin, Ji, Cong-Bin, Peng, Yi-Yuan, Zeng, Xing-Ping
Format: Article
Language:English
Subjects:
2-Bromomalonate
Coumarins
Cyclopropa[c]coumarin
Cyclopropanation
Michael-alkylation
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Summary:A convenient and efficient method for the synthesis of highly functionalized cyclopropa[c]coumarin derivatives in good to excellent yields via cascade Michael-alkylation process of 3-substituted coumarins and 2-bromomalonate was developed. Preliminary results indicated that using a chiral PTC strategy, the desired cyclopropanation product could be obtained in up to 41% ee. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.130852