Synthesis of alkylidenecyclopropanes via thermal cycloreversion of α-spirocyclopropyl-β-lactones

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 469-470

  Danheiser, Rick L ^a   Lee, Thomas W ^a   Menichincheri, Maria ^a   Brunelli, Steven ^a   Nishiuchi, Masaki ^a,b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041587817     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6134     Document Type: Article

References (27)

1. For a review on the chemistry of alkylidenecyclopropanes, see Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77.
2. (a) Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1185-1205.
3. (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 271-314.
4. (c) For more recent developments, see Lautens, M.; Ren Y. J. Am. Chem. Soc. 1996, 118, 10668 and references cited therein.
5. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707.
6. Other methods for effecting this transformation include: (a) Halazy, S.; Dumont, W.; Krief, A. Tetrahedron Lett. 1981, 22, 4737.
7. (b) Hiyama, T.; Kanakura, A.; Morizawa, Y.; Nozaki, H. Tetrahedron Lett. 1982, 23, 1279.
8. (c) Meijs, G. F.; Eichinger, P. C. H. Tetrahedron Lett. 1987, 28, 5559.
9. (d) Stafford, J. A.; McMurry, J. E. Tetrahedron Lett. 1988, 29, 2531.
10. (e) Petasis, N. A.; Bzowej, E. I. Tetrahedron Lett. 1993, 34, 943.
11. (a) Danheiser, R. L.; Nowick, J. S. J. Org. Chem. 1991, 56, 1176.
12. (b) Danheiser, R. L.; Nowick, J. S.; Lee, J. H.; Miller, R. F.; Huboux, A. H. Org. Synth. 1996, 73, 61.
13. (c) Danheiser, R. L.; Choi, Y. M.; Menichincheri, M.; Stoner, E. J. J. Org. Chem. 1993, 58, 322.
14. For related β-lactone syntheses based on phenyl esters and 1-acylbenzotriazoles, see: (a) Wedler, C.; Kunath, A.; Schick, H. J. Org. Chem. 1995, 60, 758.
15. (b) Wedler, C.; Kleiner, K.; Kunath, A.; Schick, H. Liebigs Ann. Chem. 1996, 881.
16. For a review on the synthesis and chemistry of β-lactones, see Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
17. For examples, see (a) Pinnick, H. W.; Chang, Y.-H.; Foster, S. C.; Govindan, M. J. Org. Chem. 1980, 45, 4505.
18. (b) Reissig, H.-U.; Böhm, I. J. Am. Chem. Soc. 1982, 104, 1735.
19. (c) Paquette, L. A.; Blankenship, C.; Wells, G. J. J. Am. Chem. Soc. 1984, 106, 6442.
20. (d) Häner, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1655.
21. (e) Häner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676 and references cited therein.
22. 2: C, 70.87; H, 7.32. Found C, 70.72; H, 7.31.
23. Wang, C.-H.; Cohen, S. G. J. Am. Chem. Soc. 1957, 79, 1924.
24. Prepared by reduction of the commercially available sulfonyl chloride with zinc according to the general procedure of Caesar, P. D. Organic Syntheses; Wiley: New York, 1963; Coll. Vol. IV; pp 695-697.
25. Ohta, S.; Okamoto, M. Tetrahedron Lett. 1981, 22, 3245.
26. 2: C, 72.26; H, 8.49. Found C, 72.13; H, 8.43.
27. Adam, W.; Encarnacion, L. A. A. Synthesis, 1979, 388.