De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis.
A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.
Comely
Alex C
AC
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Eelkema
Rienk
R
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000080:Acetals / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D002241:Carbohydrates; D006027:Glycosides; D011714:Pyrans; D010165:Palladium