An efficient synthesis of α-acyloxyketone by Cu(acac)2-catalyzed insertion reaction of α-diazoketone to carboxylic acid

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3757-3760

  Shinada, Tetsuro ^a   Kawakami, Tadashi ^a   Sakai, Hiroshi ^a   Takada, Ichinori ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Catalysts; Diazo compounds; Esters; Insertion reactions

Indexed keywords

ALPHA ACYLOXYKETONE; CARBOXYLIC ACID; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0032575173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00578-4     Document Type: Article

References (17)

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8. [8] For example, the hydroxyketones corresponding to 1c,e,f did not form α-acyloxyketones with Boc-amino acids using EDCI in the presence of DMAP.
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13. 2 and copper powder were reported. See references 1, 9, and 10.
14. 2 (76%, 70 °C), none (0%, 70 °C).
15. [15] 2-Cyclopentenone was a by-product due to a 1,2-hyride shift. Its yield was increased when the reaction was carried out at room temperature.
16. 2 (26.2 mg, 0.1 mmol) in toluene (3 mL) was added, dropwisely, 2-diazocyclohexanone 1a (124 mg, 1 mmol) in toluene (3 mL) at room temperature. The mixture was stirred at the same temperature for 1 h and concentrated in vacno. The residue was purified by column chromatography on silica gel to give 8 (303 mg, 84%) as a colorless oil.
17. [17] By the present method, 8 was prepared on 20 g scales.