Organocatalysis applied to carbohydrates: from roots to current developments

Abstract

Organocatalysis emerged in the last decades as a powerful tool to the synthesis complex molecules. In the field of carbohydrates, it found widespread utilization in the synthesis of rare and...

Trifluoromethyl Ketone Galactose Catalyst for Asymmetric Epoxidation: Experimental and Theoretical Model

“…Nowadays, they have been applied in several reactions, including Michael addition reaction, aldol reactions, or Morita-Baylis-Hillman reaction. [3,4] Among them, sugar-derived ketones have been employed for the synthesis of optically active epoxides. [5] In 1996, the seminal work by Shi reported that a fructose-derived chiral ketone is able to efficiently perform the asymmetric epoxidation of olefins after its in-situ conversion into a chiral dioxirane by treatment with Oxone or H 2 O 2 in basic conditions.…”

“…Organocatalysis developed as an alternative route to produce chiral molecules, and carbohydrates also emerged as chiral scaffolds for catalyst design and synthesis. Nowadays, they have been applied in several reactions, including Michael addition reaction, aldol reactions, or Morita–Baylis–Hillman reaction [3,4] . Among them, sugar‐derived ketones have been employed for the synthesis of optically active epoxides [5] .…”

Stereoselective Shi-type epoxidation with 3-oxo-4,6-O-benzylidene pyranoside catalysts: unveiling the role of carbohydrate skeletons

“…1,2 The increasing demand for scaffolds in the development of new organocatalysts has spurred researchers to explore carbohydrates with distinctive characteristics, making them promising candidates for organocatalysis. 3,4 In the last years, several ketones based on sugar skeletons have been developed to be exploited in Shi-type epoxidation. In 1996, Shi et al reported the use of a fructosederived ketone as an organocatalyst for enantioselective epoxidation of trans-olens with potassium peroxymonosulfate (Oxone) as oxidant.…”