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Updated: Dec 16, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal
Scott A Geringer1, Michael P Mannino1, Mithila D Bandara1
1Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, MO 63121, USA. demchenkoa@umsl.edu.
Abstract:
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts.
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