Abstract
Reaction of 3-acylcoumarins with α-bromoketones in the presence of a base give the cyclopropane derivatives in good stereoselectivity and moderate yield. The reaction was carried out at room temperature in mixed solvents without exclusion of moisture or air.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
For a review, see: (a) Salaun J 1989 Chem. Rev. 89 1247
Li A-H, Dai L-X and Aggarwal V K Chem. Rev. 97 2341
Reissig H-U and Zimmer R 2003 Chem. Rev. 103 1151
Pietruszka J 2003 Chem. Rev. 103 1051
Donaldson W A 2001 Tetrahedron 57 8589
Hajos Z and Parrish D R 1974 J. Org. Chem. 39 1615
Eder U, Sauer G and Wiechert R 1971 Angew. Chem. 83 492; Eder U, Sauer G and Wiechert R 1971 Angew. Chem. Int. Ed. Engl. 10 496
Dalko PI and Moisan L 2001 Angew. Chem. 113 3840; Dalko P I and Moisan L 2001 Angew. Chem. Int. Ed. 40 3726
Northrup A B and MacMillan D W C 2002 J. Am. Chem. Soc. 124 2458
Ramachary D B, Chowdari N S and Barbas III C F 2003 Angew. Chem. 115 4365; Ramachary D B, Chowdari N S and Barbas III C F 2003 Angew. Chem. Int. Ed. 42 4233
Wang J-C, Ng S-S and Krische M J 2003 J. Am. Chem. Soc. 125 3682
Wang L-C, Luis A L, Agapiou K, Jang H-Y and Krische M J 2002 J. Am. Chem. Soc. 124 2402
Frank S A, Mergott D J and Roush W A 2002 J. Am. Chem. Soc. 124 2405
Pidathala C, Hoang L, Vignola N and List B 2003 Angew. Chem. 115 2891
Pidathala C, Hoang L, Vignola N and List B 2003 Angew. Chem. Int. Ed. 42 2785
Kerr M S, de Alaniz J R and Rovis T 2002 J. Am. Chem. Soc. 124 10298
Mccoy L L 1960 J. Org. Chem. 25 2078
Mccoy L L 1962 J. Am. Chem. Soc. 27 4312
Mccoy L L and Nachtigall G W 1962 J. Org. Chem. 27 4312
Mccoy L L 1964 J. Org. Chem. 29 240
Jonczyk A and Makosza M 1976 Synthesis 387
Artaud J, Sey-den-Penne J and Viout P 1980 Synthesis 34
Widman O and Ber Dtsch 1918 Chem. Ges. 51 533
Widman O 1918 Chem. Ges. 51 907
Anka Bojilova and Nestor A Rodios 1993 Tetrahedron 49 2275
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhao, Q., Chen, M., Hui, HH. et al. High stereoselective cyclopropanation reaction of 3-acylcoumarins with α-bromoketones at room temperature. J Chem Sci 120, 391–394 (2008). https://doi.org/10.1007/s12039-008-0062-8
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-008-0062-8