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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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Published in: | Asian journal of organic chemistry 2022-01, Vol.11 (1), p.n/a |
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Main Authors: | , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 2193-5807 2193-5815 |
DOI: | 10.1002/ajoc.202100649 |