Aqueous cycloaddition using glyco-organic substrates. Facial stereoselectivity in Diels–Alder reactions of a chiral diene derived from D-glyceraldehyde

Abstract

The preparation of a new chiral, water-soluble E-diene, which could be considered as the simplest diene obtainable from the simplest sugar, is described, along with its use in cycloaddition with acrylaldehyde. Water, as the solvent, enhanced the rate of the Diels–Alder reaction, promoted complete regio- and endo-selectivity, and improved a like(anti) facial selectivity, compared with the results obtained with organic solvents.