Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides

نویسندگان

  • Carlos Palo-Nieto
  • Abhijit Sau
  • Ryan Williams
  • M Carmen Galan
چکیده

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.

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عنوان ژورنال:

دوره 82  شماره 

صفحات  -

تاریخ انتشار 2017