Abstract
We report a modified process that dichloroketene generated in situ from trichloroacetyl chloride and Zn powder reacts with unreactivate carbonyl groups to afford dichloro-β-lactones in moderate to good yields. Subse-quently, monochloro-β-lactones, β-lactones and β-hydroxy ester are obtained by dechlorination under different reac-tion conditions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Evidente A., Iacobellis N. S., Surico G., Phytochemistry, 1990 29, 1491
Thiele M., Rabe S., Hessenkemper W., Roell D., Bartsch S., Kraft F., Abraham T. E., Houtsmuller A. B., van Royen M. E., Giannis A., Ba-niahmad A., Curr. Med. Chem., 2015 22, 1156
ElBialy S. A. A., Braun H., Tietze L. F., Eur. J. Org. Chem., 2005, 2965
Einhorn A., Ber. Dtsch. Chem. Ges., 1883 16, 2208
Pommier A., Pons J. M., Synthesis, 1993, 441
Yang H. W., Romo D., Tetrahedron, 1999 55, 6403
Wang Y. C., Tennyson R. L., Romo D., Heterocycles, 2004 64, 605
Mulzer J., Bruntrup G., Chucholowski A., Angew. Chem. Int. Ed., 1979 18, 622
Adam W., Narita N., Nishizawa Y., J. Am. Chem. Soc., 1984 106, 1843
Lowe C., Pu Y. L., Vederas J. C., J. Org. Chem., 1992 57, 10
Barnett W. E., Sohn W. H., J. Chem. Soc. Chem. Commun., 1972, 472
Danheiser R. L., Nowick J. S., J. Org. Chem., 1991 56, 1176
Evans S. A. Jr., Gordon N. J., J. Org. Chem., 1993 58, 5295
Arrastia I., Lecea B., Cossio F. P., Tetrahedron Lett., 1996 37, 245
Wedler C., Ludwig R., Schick H., Pure Appl. Chem., 1997 69, 605
Hirai K., Homma H., Mikoshiba I., Heterocycles, 1994 38, 281
Yang H. W., Romo D., J. Org. Chem., 1997 62, 4
Yang H. W., Zhao C., Romo D., Tetrahedron, 1997 53, 16471
Yang H. W., Romo D., J. Org. Chem., 1998 63, 1344
Wynberg H., Staring E. G. J., J. Am. Chem. Soc., 1982 104, 166
Wynberg H., Staring E. G. J., J. Org. Chem., 1985 50, 1977
Tennyson R., Romo D., J. Org. Chem., 2000 65, 7248
Cater M. A., J. Org. Chem., 1996 61, 8006
Tamai Y., Someya M., Fukumoto J., J. Chem. Soc., Perkin Trans. 1, 1994, 1549
Tamai Y., Yoshiwara H., Someya M., J. Chem. Soc. Chem. Commun., 1994, 2281
Dymock B. W., Kocienski P. J., Pons J. M., J. Chem. Soc. Chem. Commun., 1996, 1053
Romo D., Harrision P. H., Bioorg., Med. Chem., 1998 6, 1255
Zipp G. G., Nelson S. G., Org. Lett., 2002 4, 1823
Nelson S. G., Kim B. K., J. Am. Chem. Soc., 2000 122, 9318
Nelson S. G., Wan Z. H., Tetrahedron Lett., 1999 40, 6541
Evans D. A., Janey J. M., Org. Lett., 2001 3, 2125
Arjona O., Pradilla R. F., Tetrahedron Lett., 1986 27, 5505
Arjona O., Pradilla R. F., Tetrahedron, 1988 44, 1235
Palorno C., Miranda J. l., Cuevas C., Odriozola J. M., J. Chem. Soc. Chem. Commun., 1995, 1735
Hyatt J. A., Raynolds P. W., Org. React., 1994 45, 159
Brady W. T., Patel A. D., J. Heterocyclic Chem., 1971 8, 739
Snider J. R., Entrekin J. T., Snowden T. S., Dolliver D., Synthe-sis(Germany), 2013 45, 1899
Mulzer J., Pointner A., Tetrahedron Lett., 1995 36, 3679
Yokoyama R., Ito S., Monita. N., Watanabe M., Harade N., Kabuto C., Morita N., J. Chem. Soc., Perkin Trans 1, 2001, 2257
Brown D. G., Bernstein P. R., Groblewski T., J. Med. Chem., 2014 57, 733
Matsuo J., Kawano M., Ishibashi H., Org. Lett., 2010 12, 3960
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the National Natural Science Foundation of China(No.21272126) and the Natural Science Foundation of Tianjin, China(No.18JCYBJC28400).
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Dong, X., Zhang, C., Xu, J. et al. Formation of β-Lactones by [2+2] Cycloaddition of Dichloroketene with Unreactive Carbonyl Compounds. Chem. Res. Chin. Univ. 34, 736–743 (2018). https://doi.org/10.1007/s40242-018-8088-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-018-8088-z