Projects per year
Abstract
A practical approach for the ∝-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocataly-sis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors and its versatility is exempli-fied in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chi-ral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.
Original language | English |
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Pages (from-to) | 407–414 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 82 |
Issue number | 1 |
Early online date | 22 Dec 2016 |
DOIs | |
Publication status | Published - 6 Jan 2017 |
Keywords
- Cooperative catalysis
- organocatalysis
- chiral phosphoric acids
- chiral acetals
- stereoselectivity
- deoxyglycosides
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Dive into the research topics of 'Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides'. Together they form a unique fingerprint.Projects
- 2 Finished
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
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Reworking of Novel tools for Glycoscience
Galan, M. C. (Principal Investigator)
31/03/12 → 30/08/17
Project: Research