Alkylation of ethyl pyruvate via reductive coupling of alkenes and ethyl 2-(Benzenesulfonylamino)acrylate

Chimia

Volumn 59, Issue 3, 2005, Pages 109-110

  Darmency, Vincent ^b   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b NONE

Author keywords

Alkylation; Enamides; Hydroboration; Organoboranes; Radical reactions; Sulfonamides

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE; ORGANOBORON DERIVATIVE; PYRUVIC ACID DERIVATIVE; SULFONE DERIVATIVE;

ALKYLATION; ALLYLATION; ANALYTIC METHOD; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CONFERENCE PAPER; REACTION ANALYSIS;

EID: 17444363040     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942905777676722     Document Type: Conference Paper

References (10)

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9. Typical experimental procedure: Catecholborane (533 μl, 5.0 mmol) was added dropwise at 0°C to a solution of (+)-α-pinene (317 μl;, 2.0 mmol) and N,N-dimethylacetamide (18 μl, 0.2 mmol) in dry 1,2-dichloroethane (2 ml) under stirring and inert atmosphere. The resulting colorless solution was heated under reflux for 5 h. The reaction mixture was carefully quenched at 0°C with dry methanol (200 μl) and stirred 15 min at room temperature. Ethyl 2-(benzenesulfonamino)acrylate (255 mg, 1.0 mmol) was added followed by di-tert-butylhyponitrite (9 mg). The resulting yellow mixture was stirred under reflux for 4 h until a black coloration appeared. Every 1 h, a portion of di-tert-butylhyponitrite (9 mg) was added. The alkylated pyruvate (80 mg, 32%) was obtained after purification by flash chromatography (hexane/ethyl acetate 95:5).
10. W.R. Hertler, J. Org. Chem. 1974, 39, 3219.