Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 52, Pages 16823-16827Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202446
Keywords
homogeneous catalysis; diastereoselectivity; propargylation; ruthenium; transfer hydrogenation
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Funding
- Robert A. Welch Foundation [F-0038]
- NSF [CHE-1008551]
- Government of Canada's Banting Postdoctoral Fellowship Program
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1008551] Funding Source: National Science Foundation
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Under the conditions of ruthenium-catalyzed transfer hydrogenation employing isopropanol as a source of hydrogen, isopropoxy-substituted enyne 1b and aldehydes 3a-3l engage in reductive coupling to provide products of propargylation 4a-4l with good to complete levels of anti-diastereoselectivity. The unprotected tertiary hydroxy moiety of isopropoxy enyne 1b is required to enforce diastereoselectivity. Deuterium-labeling studies corroborate reversible enyne hydrometalation in advance of carbonyl addition. As demonstrated in the conversion of 4f-h and 4k to 5f-h and 5k, the isopropoxy group of the product is readily cleaved upon exposure to aqueous sodium hydroxide to reveal the terminal alkyne.
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