α,β‐Unsaturated 2‐Ketoglycosides via Pd‐Catalyzed Carbonylative Heck Reaction of 2‐Iodoglycals

The synthesis of C‐glycosides is of great importance in the field of carbohydrate chemistry given its ubiquity in biologically active molecules. Herein, we describe a protocol for the Pd‐catalyzed carbonylative Heck reaction of activated olefins and 2‐iodoglycals. A variety of α,β‐unsaturated 2‐keto...

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Published in:European journal of organic chemistry 2020-08, Vol.2020 (32), p.5220-5226
Main Authors: Darbem, Mariana P., Esteves, Henrique A., Oliveira, Isadora M., Stefani, Hélio A.
Format: Article
Language:English
Subjects:
Activated carbon
Alkenes
Carbohydrates
Carbonylation
Carbonyls
Glycosides
Heck reaction
Palladium
Synthetic methods
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description The synthesis of C‐glycosides is of great importance in the field of carbohydrate chemistry given its ubiquity in biologically active molecules. Herein, we describe a protocol for the Pd‐catalyzed carbonylative Heck reaction of activated olefins and 2‐iodoglycals. A variety of α,β‐unsaturated 2‐ketoglycosides were obtained in up to 89 % yield using d‐glucal, d‐galactal, d‐xylal, and l‐arabinal derivatives. The synthesis of biologically relevant C‐ketoglycosides, found in many important natural products and medicinally active molecules is reported. This strategy allows to connect a series of glycal units to activated olefins via the Pd‐catalyzed carbonylative Heck cross‐coupling reaction.
doi_str_mv 10.1002/ejoc.202000846
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subjects Activated carbon
Alkenes
Carbohydrates
Carbonylation
Carbonyls
Glycosides
Heck reaction
Palladium
Synthetic methods
title α,β‐Unsaturated 2‐Ketoglycosides via Pd‐Catalyzed Carbonylative Heck Reaction of 2‐Iodoglycals
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