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Cooperative Bronsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides.

ABSTRACT: A practical approach for the ?-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.

SUBMITTER: Palo-Nieto C

PROVIDER: S-EPMC5309864 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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

Palo-Nieto Carlos C Sau Abhijit A Williams Ryan R Galan M Carmen MC

The Journal of organic chemistry 20161222 1

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 ...[more]

PMID: 28004941

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