Organocatalytic enantioselective a-alkylation of cyclic ketones by SN1-type reaction of alcohols

Bulletin of the Korean Chemical Society

Volumn 32, Issue 4, 2011, Pages 1125-1126

  Lee, Hyun Joo ^a   Kang, Seung Hee ^a   Kim, Dae Young ^a  

^a Soonchunhyang University   (South Korea)

Author keywords

Alkylation; Carbocations; Enamine catalysis; Nucleophilic substitution; Organocatalysis

Indexed keywords

EID: 79954575705     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.4.1125     Document Type: Article

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39. General procedure for the organocatalytic ?-alkylation of cyclic ketones 1: To a stirred solution of bis(4-dimethylaminophenyl)- methanol (2, 81.9 mg, 0.3 mmol), catalyst V (12.6 mg, 0.06 mmol), triphenyl phosphine (23.4 mg, 0.09 mmol), and TFA (6.6 mL, 0.09 mmol) in diethyl ether (1.2 mL) was added ketones 1 (1.5 mmol) at room temperature. Reaction mixture was stirred for 15-24 h at room temperature, concentrated, and purified by flash column chromatography (EtOAc/hexane: 1/3) to afford the alkylated product 3.