Journal
ORGANIC LETTERS
Volume 15, Issue 12, Pages 3030-3033Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4012184
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Funding
- Japan Science and Technology Agency [AS242Z01398Q]
- Japan Society for the Promotion of Science (JSPS) [24350042]
- MEXT (Japan) program Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions of Hokkaido University
- Grants-in-Aid for Scientific Research [25410105] Funding Source: KAKEN
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Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru(OTf)(TsDPEN)(eta(6)-p-cymene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact In most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H-2. The mode of enantioselection is elucidated with the transition state models directed by the CH/pi attractive interaction between the substrate and the catalytic species.
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