Journal
ORGANIC LETTERS
Volume 12, Issue 20, Pages 4624-4627Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1019629
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- AstraZeneca
- National Institutes of Health (NIH) [NIH CA53604]
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Allenylsilanes are used as carbon nucleophiles in highly stereoselective Lewis acid-promoted C-glycosidations, resulting in the introduction of an internal alkyne with an adjacent stereocenter. Both achiral and chiral allenylsilanes form the desired products with high diastereoselectivity, where the nucleophile adds exclusively to the alpha-face of the intermediate oxonium ion. Reactions with glucal and galactal afford dihydropyran products, while reactions with a ribose derivative yield dihydrofuran products.
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