N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution of Pyranones

Changgui Zhao; Fangyi Li; Jian Wang

doi:10.1002/anie.201508205

N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution of Pyranones

Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1820-4. doi: 10.1002/anie.201508205. Epub 2015 Nov 6.

Authors

Changgui Zhao^{1

2}, Fangyi Li¹, Jian Wang^{3

4}

Affiliations

¹ Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084, China.
² Tsinghua-Peking Centre for Life Sciences, Beijing, 100084, China.
³ Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084, China. [email protected].
⁴ Tsinghua-Peking Centre for Life Sciences, Beijing, 100084, China. [email protected].

PMID: 26546390
DOI: 10.1002/anie.201508205

Abstract

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.

Keywords: N-heterocyclic carbenes; catalysis; dynamic kinetic resolution; glycosylation; pyranones.

Publication types

Research Support, Non-U.S. Gov't