Organocatalytic asymmetric michael addition of 1,3-cyclohexanedione to β,-unsaturated a-keto esters

Bulletin of the Korean Chemical Society

Volumn 33, Issue 11, 2012, Pages 3537-3538

  Lee, Hyun Joo ^a   Kim, Dae Young ^a  

^a Soonchunhyang University   (South Korea)

Author keywords

1,3 Cyclohexanedione; Asymmetric catalysis; Michael addition; Organocatalysis

Indexed keywords

EID: 84870020985     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2012.33.11.3537     Document Type: Article

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56. General procedure for asymmetric conjugate addition 1,3-cyclohexanedione (1) to ß,?-unsaturated a-keto esters 2: To a stirred solution of ß,?-unsaturated a-keto esters 2 (0.5 mmol), binaphthyl-modified organocatalyst (II, 1.6 mg, 0.0025 mmol) in toluene (2 mL) was added 1,3-cyclohexanedione (1, 56.0 mg, 0.5 mmol) at-40 oC. The reaction mixture was stirred at-40 oC for a specified reaction time period. The reaction mixture was purified by column chromatography on silica gel, eluted by hexane/EtOAc = 1:1 to give the desired product 3.