Author(s):
Dias, T. A. 
; Durães, C. ; Esteves, Ana Paula ; Medeiros, Maria José ; Pletcher, D.
Date: 2013
Persistent ID: http://hdl.handle.net/1822/25659
Origin: RepositóriUM - Universidade do Minho
Document details
Reductive intramolecular cyclization of D-glucose-based unsaturated substrates ...
Description
Radical cyclisation continues to be a central methodology for the preparation of natural products containing heterocyclic rings. Hence, some electrochemical results obtained by cyclic voltammetry and controlled-potential electrolysis in the study of electroreductive intramolecular cyclisation of ethyl (2S, 3R)-2- bromo-3-propargyloxy-3-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosiloxy) propanoate (1) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetra-decane)nickel(I), [Ni(tmc)]+, electrogenerated at glassy carbon cathodes in ethanol and ethanol/water mixtures containing tetraalkylammonium salts, are presented. During controlled-potential electrolyses of solutions containing [Ni(tmc)]2+ and acetylated D-glucose-based bromo propargyl ester (1) catalytic reduction of the latter proceeds via one-electron cleavage of the carbon–bromine bond to form a radical intermediate that undergoes cyclization to afford the substituted tetrahydrofurans.
Radical cyclisation continues to be a central methodology for the preparation of natural products containing heterocyclic rings. Hence, some electrochemical results obtained by cyclic voltammetry and controlled-potential electrolysis in the study of electroreductive intramolecular cyclisation of ethyl (2S, 3R)-2- bromo-3-propargyloxy-3-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosiloxy) propanoate (1) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetra-decane)nickel(I), [Ni(tmc)]+, electrogenerated at glassy carbon cathodes in ethanol and ethanol/water mixtures containing tetraalkylammonium salts, are presented. During controlled-potential electrolyses of solutions containing [Ni(tmc)]2+ and acetylated D-glucose-based bromo propargyl ester (1) catalytic reduction of the latter proceeds via one-electron cleavage of the carbon–bromine bond to form a radical intermediate that undergoes cyclization to afford the substituted tetrahydrofurans.
Document Type
Article
Language English
Language English
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