Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3581-3584

  Choudhury, Prabir K ^a   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; CARBONYL DERIVATIVE; INDIUM; LACTONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032554993     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00554-1     Document Type: Article

References (23)

1. See, for instance: (a) Ashida, K.; Sakakibara, Y.; Maramatsu, I.; Fujiwara, M. Jpn. J. Pharmacol. 1982, 32, 183P.
2. 5).
3. For reviews, see: (a) Grieco, P. A. Synthesis 1975, 67-82.
4. (b) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110.
5. Representative examples are: (a) Mattes, H.; Benezra, C. Tetrahedron Lett 1985, 26, 5697-5698.
6. (b) Still, I. W. J.; Drewery, M. J. J. Org. Chem. 1989, 54, 290-295.
7. (c) Sidduri, A. R.; Knochel, P. J. Am. Chem. Soc. 1992, 114, 7579-7581.
8. See, for instance: (a) Uneyama, K.; Ueda, K.; Torii, S. Chem. Lett. 1986, 1201-1202.
9. (b) Talaga, P.; Schaeffer, M.; Benezra, C.; Stampf, J.-L. Synthesis 1990, 530.
10. See, for instance: Okuda, Y.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Chem. Lett. 1985, 481-484.
11. 2 in order to get the expected α-methylene- γ-butyrolactone. See, for instance: Carlson, R. M. Tetrahedron Lett. 1978, 111-114.
12. 2
13. For an excellent review, see: (a) Cintas, P. Synlett 1995, 1087-1096.
14. 8c see: (b) Bernardelli, P.; Paquette, L. A. J. Org. Chem. 1997, 62, 8284-8285.
15. (c) Yadav, J. S.; Srinivas, D.; Reddy, G. S.; Bindu, K. H. Tetrahedron Lett. 1997, 38, 8745-8748.
16. 9b,c and shows fungitoxic properties. (a) Cavallilo, C. J.; Haskell, T. H. J. Am. Chem. Soc. 1946, 68, 2332-2334.
17. (b) Brongersma-Oosterhoff, U. W. Recl. Trav. Chim. Pays-Bas 1967, 86, 705-708;
18. Chem. Abstr. 1967, 67, 61038y.
19. (c) Bergman, B. H. H.; Beijersbergen, J. C. M.; Overeem, J. C.; Sijpesteijin, A. K. Recl. Trav. Chim. Pays-Bas 1967, 86, 709-714;
20. Chem. Abstr. 1967, 67, 71117n.
21. For a practical synthesis, see: (d) Grieco, P. A.; Pogonowski, C. S. J. Org. Chem. 1974, 39, 1958-1959.
22. f 0.38 (hexane/ethyl acetate: 1/1).
23. See, for instance: Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538-2542 and references cited therein.