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Organocatalyzed Asymmetric Tandem Intramolecular oxa‐Michael Addition/Electrophilic Thiocyanation: Synthesis of Chiral α‐Thiocyanato Flavanones

An efficient bifunctional cinchona alkaloids‐catalyzed asymmetric tandem intramolecular oxa‐Michael addition/electrophilic thiocyanation of alkylidene β‐ketoesters with N‐thiocyanatosuccinimide (NTS) was developed. A series of chiral α‐thiocyanato flavanones containing two vicinal stereocenters incl...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2022-01, Vol.11 (1), p.n/a
Main Authors: Gao, Yong, Fu, Zhenda, Wu, Di, Yin, Hongquan, Chen, Fu‐Xue
Format: Article
Language:English
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Summary:An efficient bifunctional cinchona alkaloids‐catalyzed asymmetric tandem intramolecular oxa‐Michael addition/electrophilic thiocyanation of alkylidene β‐ketoesters with N‐thiocyanatosuccinimide (NTS) was developed. A series of chiral α‐thiocyanato flavanones containing two vicinal stereocenters including an all‐carbon quaternary center were prepared in good yields with excellent diastereo‐ and enantioselectivities (up to 97% ee) under mild conditions, and a successful scale up preparation of our protocol was also demonstrated. An efficient bifunctional cinchona alkaloids‐catalyzed asymmetric tandem intramolecular oxa‐Michael addition/electrophilic thiocyanation of alkylidene β‐ketoesters with N‐thiocyanatosuccinimide (NTS) was developed. A series of chiral α‐thiocyanato flavanones containing two vicinal stereocenters including an all‐carbon quaternary center were prepared in good yields with excellent diastereo‐ and enantioselectivities (up to 97% ee) under mild conditions.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100649