N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution of Pyranones

• Published in: Angewandte Chemie International Edition Vol. 55; no. 5; pp. 1820 - 1824
• Main Authors: Zhao, Changgui, Li, Fangyi, Wang, Jian
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 26.01.2016; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: catalysis; Chemistry; Chemistry, Multidisciplinary; dynamic kinetic resolution; Esterification; Esters; glycosylation; N-heterocyclic carbenes; Natural products; Physical Sciences; pyranones; Reaction products; Science & Technology; Sugar; ASYMMETRIC-SYNTHESIS; OLIGOSACCHARIDES; ENANTIOSELECTIVE SYNTHESIS; DE-NOVO SYNTHESIS; ALPHA,BETA-UNSATURATED ALDEHYDES; catalysis; glycosylation; ALPHA; pyranones; SECONDARY ALCOHOLS; ESTERS; RACEMIZATION; EFFICIENT; dynamic kinetic resolution; N-heterocyclic carbenes

The dynamic kinetic resolution of 6‐hydroxypyranones with enals or alkynals through an asymmetric redox esterification is catalyzed by a chiral N‐heterocyclic carbene. The resulting esters are obtained in good to high yields and with high levels of enantio‐ and diastereocontrol. The reaction product...