Glyco-organic substrates in organic synthesis. Preparation of a water soluble butadienyl-ether and its use in aqueous cycloaddition.

Abstract A chiral water-soluble butadienyl-ether containing free glucose as hydrophilic moiety was synthesized and used in aqueous cycloaddition reaction with methacrolein to afford through pure endo transition state, only two diastereoisomers from which the sugar could be removed by enzymatic hydrolysis.