Related Experiment Video
Updated: Jan 30, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Mannich Reactions of Carbohydrate Derivatives with Ketones To Afford Polyoxy-Functionalized Piperidines
Lingaiah Maram1, Fujie Tanaka1
1Chemistry and Chemical Bioengineering Unit , Okinawa Institute of Science and Technology Graduate University , 1919-1 Tancha , Onna , Okinawa 904-0495 , Japan.
Abstract:
Mannich reactions of carbohydrate derivatives with ketones that afford polyoxy-functionalized piperidines are reported. Ketone nucleophiles (enamines/enolates) were generated in the presence of the amines used for the formation of the iminium ions of sugar derivatives with or without an additive. Conditions to preferentially generate piperidine derivatives rather than tetrahydrofurans were identified. Products from the reactions of allyl ketones were readily transformed to bicyclic piperidines.
Related Concept Videos
Chemistry of Carbohydrates
Functional Groups
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard...
What are Carbohydrates?
Carbohydrate Digestion
The Derivative as a Function

