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Updated: Aug 18, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Chemoenzymatic synthesis of carbasugars from iodobenzene
Derek R Boyd1, Narain D Sharma, Nuria M Llamas
1Centre for Theory and Application of Catalysis, School of Chemistry, The Queen's University of Belfast, Belfast, UKBT9 5AG.
Abstract:
The versatile enantiopure cis-dihydrodiol metabolite 1, formed by bacterial metabolism of iodobenzene, has been used for the synthesis of the pyranose carbasugars (pseudosugars) carba-beta-D-altropyranose 2, carba-alpha-L-galactopyranose 3, carba-beta-D-idopyranose 4 and carba-beta-L-glucopyranose 5. Substitution of the iodine atom by a carbomethoxy group, stereoselective catalytic hydrogenation of an alpha,beta-unsaturated ester, and regioselective inversion of one or two allylic chiral centres are the key steps used in the synthesis of carbasugars 2-5. The relative and absolute configurations of compounds 2-5 were established by a combination of stereochemical correlation, X-ray crystallography and 1H-NMR spectroscopy.
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