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Enantioselective α-chlorination of β-oxo esters catalyzed by chiral diterpenoid alkaloid derivatives
Institution:1. School of Pharmacy, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa;2. Division of Clinical Pharmacology, Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory 7925, South Africa;1. Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic;2. Department of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 66 Košice, Slovak Republic;3. Division of Biological Sciences, Graduate School of Science, Frontier Research Center for Post-Genomic Science and Technology, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan;4. Department of Analytical Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic;1. University of Texas at Austin, Austin, TX 78712, USA;2. Department of Chemistry, University of Texas at Austin, Austin, TX 78746, USA
Abstract:Easily accessible diterpenoid alkaloid derivatives have been used as organocatalysts in the enantioselective α-chlorination of β-oxo esters. The treatment of β-oxo esters with N-chlorophthalimide (NCP) as a chlorine source under mild reaction conditions afforded the corresponding α-chlorinated β-oxo esters in excellent yields (up to 98%) and with moderate enantioselectivities (up to 68% ee) in 30 min.
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