Related Experiment Video
Updated: Sep 20, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
One-pot conversion of glycals to cis-1,2-isopropylidene-alpha-glycosides
Gregory J S Lohman1, Peter H Seeberger
1Massachusetts Institute of Technology, 77 Massachusetts Avenue 18-292, Cambridge, Massachusetts 02139, USA.
Abstract:
Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-alpha-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl(2)-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-alpha-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.
Related Concept Videos
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

