Pd(II)-mediated carbonylation of propargylic acetates leading to γ- acetoxy-β-methoxy-α,β-unsaturated esters

Synlett

Volumn , Issue 2, 2000, Pages 217-218

  Okumoto, Hiroshi ^a   Nishihara, Satoshi ^a   Nakagawa, Hiroko ^a   Suzuki, Akira ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

Acetylene; Carbonylations; Catalysis; Palladium; keto ester

Indexed keywords

ACETYLENE; CARBON MONOXIDE; ESTER; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STOICHIOMETRY; TEMPERATURE;

EID: 0033964272     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6509     Document Type: Article

References (7)

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4. Li, J.; Jiang, H.; Feng, A.; Jia, L. J. Org. Chem. 1999, 64, 5984.
5. Murry, T. F.; Samsel, E. G.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1981, 703, 7520.
6. 3 (1 ml) and MeOH (4 ml) was stirred under CO atmosphere (balloon) at the temperature indicated in the Table. After the starting material was consumed, the reaction mixture was passed through short florisil column and the filtrates were concentrated. The residue was chromatographed to obtain the ester 2.
7. 2 and ensuing 1,4-addition of MeOH were also conceivable (Scheme 4). (formula presented) Scheme 4 However, the process was ruled out by an experiment using internal acetylene 9 (Scheme 5). Carbonylation of 9 in a similar manner gave unsaturated ester 10 and β-ketoester 11, although the reaction was rather slow in comparison with terminal acetylenes. (formula presented) Scheme 5