School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
J Org Chem. 2017 Jan 6;82(1):407-414. doi: 10.1021/acs.joc.6b02498. Epub 2016 Dec 22.
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.
已开发出一种使用协同 Brønsted 酸型有机催化的α-立体选择性合成去氧糖苷的实用方法。该方法对各种糖苷供体和受体具有耐受性,其多功能性在一锅法合成三糖中得到了例证。机理研究表明,硫脲通过氢键诱导手性酸的酸增强是提高反应速率和产率的关键,而立体控制取决于酸的手性。