Journal
ORGANIC LETTERS
Volume 22, Issue 6, Pages 2191-2195Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00348
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Funding
- SERB (DST, New Delhi) [ECR/2016/000262]
- IITG
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The conjugate acid of the bulky base 2,4,6-tri-tert-butylpyridine, under mild conditions, catalyzes the synthesis of silyl-protected 2-deoxy-hemiacetals and their dimerized products from glycals at varying concentrations of water. The criticality of the concentration of water in the reaction outcome is indicative of a unique mechanistic pathway for the bulky pyridine salt and not via the general Bronsted acid mechanism. The various silyl-protected hemiacetals thus synthesized were successfully utilized in the stereoselective synthesis of both alpha and beta glycosides.
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