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. 2017 Jan 6;82(1):407-414.
doi: 10.1021/acs.joc.6b02498. Epub 2016 Dec 22.

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

Carlos Palo-Nieto  1 , Abhijit Sau  1 , Ryan Williams  1 , M Carmen Galan  1
Affiliations

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

Carlos Palo-Nieto et al. J Org Chem. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Proposed Cooperative Acid/Thiourea-Catalyzed Synthesis of Deoxyglycosides
Scheme 2
Scheme 2. One-Pot Trisaccharide Synthesis
Scheme 3
Scheme 3. Proposed Mechanism
See this image and copyright information in PMC

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