Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 19, Pages 8095-8099Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2014142
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Funding
- National Natural Science Foundation of China [20972147, 20732006]
- National Basic Research Program of China (973 Program) [2010CB833300]
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A range of ketones and aldehydes smoothly undergo asymmetric S(N)1 alpha-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent yields and with good enantioselectivity. This chemistry has been successfully extended to the asymmetric desymmetrization of 4-substituted cyclohexanones, which exhibits greater than 99:1 diastereoselectivity and good enantioselectivity.
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