Chiral catalyst-directed site-selective functionalization of hydroxyl groups in carbohydrates

GRAPHICAL ABSTRACT

ABSTRACT

Carbohydrates perform essential roles in living organisms. Recently, a series of breakthroughs emerged in chiral catalyst-directed site-selective functionalization of carbohydrates. In this review site-selective functionalization of cis-diols, trans-diols and others mediated by chiral catalysts was discussed. The reaction types covered are mainly acylation, acetalization, glycosidation, thiocarbonylation, silylation, phosphorylation, sulfonylation, and so on. Some important site-selective methodologies used in the synthesis of saccharides are also elaborated.

KEYWORDS:

• Site-selectivity
• chiral catalyst
• functionalization
• hydroxyl groups

Funding

This work was supported by grants from the Fundamental Research Funds for the Central Universities (No. DUT16RC(3)070), China Postdoctoral Science Foundation (No. 2017M611216) and National Natural Science Foundation of China (Nos. 21702025, 51703018).

Additional information

Notes on contributors

Wangze Song

Wangze Song received his B.S. in chemistry from Nankai University, where he worked in Professor Chi Zhang's laboratory. He obtained his M.S. in chemistry from Zhejiang University under the supervision of Professors Yanguang Wang and Ping Lu. He received his Ph.D. in 2016 from the University of Wisconsin-Madison, worked with Professor Weiping Tang. He is currently an Associate Professor at Dalian University of Technology. His group is interested in developing new synthetic methods, carbohydrate synthesis and medicinal chemistry.

Nan Zheng

Nan Zheng was born in Changchun, China. She obtained her B.S. in polymer science from Dalian University of Technology, where she worked in Professor Yang Li's laboratory. She received her Ph.D. in materials science from University of Illinois at Urbana-Champaign under the supervision of Professor Jianjun Cheng. She joined the faculty at Dalian University of Technology in 2016 after her postdoctoral study at Texas A&M University.