title: Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides.
abstract: A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Carlos
authors.initials: C
authors.lastname: Palo-Nieto
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Sau
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Ryan
authors.initials: R
authors.lastname: Williams
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: M Carmen
authors.identifier: 0000-0001-7307-2871
authors.initials: MC
authors.lastname: Galan