Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 35, Pages 14864-14870Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c07634
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Funding
- NSF of China [21672075]
- Instrumental Analysis Center of Huaqiao University
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In this work, we describe a Catellani-type C-H glycosylation to provide rapid access to various highly decorated alpha-C-(hetero)aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside-pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an S(N)1 pathway.
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