Journal
ORGANIC LETTERS
Volume 24, Issue 23, Pages 4135-4139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01243
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Funding
- U.S. Army Research Office (ARO) [W911NF-15-2-0119]
- National Research Council
- National Institute of General Medical Science of the National Institutes of Health [R01GM130693]
- National Institutes of Health [3R01GM130693-03S1]
- National Science Foundation [CHE-0922858]
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A novel diastereoselective, Lewis acid catalyzed 1,6-difunctionalization reaction of galactose and mannose derivatives has been developed using sequential nucleophile additions. The formation of a 3,6-anhydrosugar intermediate was found to be crucial for the 1,6-site-selectivity, and the reactivity of starting materials was influenced by the differences in basicity and stereoelectronic stabilization. The nucleophilicity parameter values of Mayr helped in predicting the most suitable reaction conditions for specific nucleophiles.
A novel diastereoselective, Lewis acid catalyzed 1,6difunctionalization of galactose and mannose derivatives has been developed in one pot, via sequential nucleophile additions. Our studies point to the formation of a 3,6-anhydrosugar intermediate as key to the 1,6-site-selectivity. Starting material-specific reactivity occurs when competitive ring-opening C-O cleavage is possible, owed to basicity and stereoelectronic stabilization differences. Lastly, Mayr nucleophilicity parameter values helped predict which reaction conditions would be most suitable for specific nucleophiles.
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