A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives

…, J Thorhauge, RG Hazell, KA Jørgensen

Index: Audrain, Helene; Thorhauge, Jacob; Hazell, Rita G.; Jorgensen, Karl Anker Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4487 - 4497

Full Text: HTML

Citation Number: 140

Abstract

A catalytic enantioselective inverse-electron demand hetero-Diels-Alder reaction of α, β- unsaturated carbonyl compounds with electron-rich alkenes catalyzed by chiral bisoxazolines in combination with Cu (OTf) 2 as the Lewis acid is presented. The reaction of γ-substituted β, γ-unsaturated α-keto esters with vinyl ethers and various types of cis- disubstituted alkenes proceeds in good yield, high diastereoselectivity, and excellent ...