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
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201508205

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 products are further derivatized to obtain functionalized sugar derivatives and natural products. Sweet products: The dynamic kinetic resolution of 6‐hydroxypyranones with enals or alkynals through an asymmetric redox esterification is catalyzed by a chiral N‐heterocyclic carbene (NHC). The resulting esters are obtained in good to high yields and with high levels of enantio‐ and diastereocontrol.