Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Lactols for De Novo Synthesis of Carbohydrate.
The control of the stereochemistry at the anomeric position is still one of the major challenges of synthetic carbohydrate chemistry. We have developed a new strategy consisting of a chiral catalyst-directed acylation followed by a palladium-catalyzed glycosidation to achieve high α- and β-stereoselectivity on the anomeric position. The former process involves a dynamic kinetic diastereoselective acylation of lactols derived from Achmatowicz rearrangement, while the latter is a stereospecific palladium-catalyzed allylic alkylation.
School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
Hao-Yuan
HY
Wang
School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
Ka
K
Yang
School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
Dan
D
Yin
School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
Can
C
Liu
Department of Chemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Daniel A
DA
Glazier
School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.|Department of Chemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Weiping
W
Tang
D000215:Acylation; D000478:Alkylation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D002241:Carbohydrates; D007783:Lactones; D010165:Palladium