K2CO3-catalyzed Michael addition-lactonization reaction of 1,2-allenyl ketones with electron-withdrawing group substituted acetates. An efficient synthesis of α-pyrone derivatives

Organic Letters

Volumn 4, Issue 4, 2002, Pages 505-507

  Ma, Shengming ^a   Yin, Shaohu ^b   Li, Lintao ^a   Tao, Fenggang ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; LACTONE; POTASSIUM; POTASSIUM CARBONATE; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETATES; CARBONATES; CATALYSIS; INDICATORS AND REAGENTS; KETONES; LACTONES; POTASSIUM; PYRONES; STEREOISOMERISM;

EID: 0037148995     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0170859     Document Type: Article

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22. For some of our most recent work in this area, see: Ma, S.; Zhang, J. Chem. Commun. 2000, 117. Ma, S.; Li, L. Org. Lett. 2000, 2, 941. Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1419. Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495. Ma, S.; Xie, H. Org. Lett. 2000, 2, 3801. Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893. Ma, S. S.; Gao, W. Tetrahedron Lett. 2000, 41, 8933. Ma, S.; Wu, S. Chem. Commun. 2001, 441. Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193.
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31. For the synthesis of α-pyrone derivatives via the reaction of methyl cyano-, aceto-, or methoxycarbonyl acetate through the possible intermediate of allenyl ketones in low yields, see: Sugita, T.; Mimura, H.; Ito, H. Chem. Express 1987, 2, 37. For an earlier example of synthesis of α-pyrones from allenes, see: Mirzabekyants, N. S.; Cheburkov, Y. A.; Knunyants, I. L. Izv. Akad. Nauk SSSR, Ser. Khim. 1977, 2517.
32. 3 in 1 mL of acetone was heated to reflux with stirring. After the reaction was complete (monitored by TLC, eluent = 6:1 hexane/ethyl acetate), the solvent was evaporated and the crude product was purified by chromatography on silical gel (6:1 hexane/ethyl acetate) to afford 199 mg (79%) of 3a.