Lewis acid catalyzed reactions of methylenecyclopropylcarbinols with acetals for the construction of 3-oxabicyclo[3.1.0]hexane derivatives

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4551-4554

  Shao, Li Xiong ^a,b   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b WENZHOU UNIVERSITY   (China)

Author keywords

3 Oxobicyclo 3.1.0 hexane; Acetals; Lewis acid; Methylenecyclopropylcarbinols; Prins type reaction

Indexed keywords

3 OXABICYCLO[3.1.0]HEXANE; ACETAL; HEXANE; LEWIS ACID; METHANOL DERIVATIVE; METHYLENECYCLOPROPYLCARBINOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; PRINS REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION OPTIMIZATION; RING CLOSING METATHESIS;

EID: 77953123626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.072     Document Type: Article

References (39)

1. For the synthesis of MCPs, see:
2. Brandi A., and Goti A. Chem. Rev. 98 (1998) 589-635
3. In: de Meijere A. (Ed). Houben Weyl: Carbocyclic Three-Membered Ring Compounds Vol. E17a-c (1996), Thieme, Stuttgart
4. For some reviews, see:
5. Nakamura I., and Yamamoto Y. Adv. Synth. Catal. 344 (2002) 111-129
6. Brandi A., Cicchi S., Cordero F.M., and Goti A. Chem. Rev. 103 (2003) 1213-1270
7. Rubin M., Rubina M., and Gevorgyan V. Chem. Rev. 107 (2007) 3117-3179
8. For a recent review on the Lewis acid catalyzed ring-opening reactions of MCPs, see:. Shao L.-X., and Shi M. Curr. Org. Chem. 11 (2007) 1135-1153 and references cited therein
9. For some selected papers on the Lewis acid catalyzed cycloaddition reactions of MCPs, see:
10. Shi M., Shao L.-X., and Xu B. Org. Lett. 5 (2003) 579-582
11. Shao L.-X., and Shi M. Adv. Synth. Catal. 345 (2003) 963-966
12. Shi M., Xu B., and Huang J.-W. Org. Lett. 6 (2004) 1175-1178
13. Shao L.-X., Xu B., Huang J.-W., and Shi M. Chem.-Eur. J. 12 (2006) 510-517
14. Zhu Z.-B., Shao L.-X., and Shi M. Eur. J. Org. Chem. (2009) 2576-2580
15. For some selected papers from Kilburn's group, see:
16. Peron G.L.N., Norton D., Kitteringham J., and Kilburn J.D. Tetrahedron Lett. 42 (2001) 347-349
17. Patient L., Berry M.B., Coles S.J., Hursthouse M.B., and Kilburn J.D. Chem. Commun. (2003) 2552-2553
18. Rajamaki S., and Kilburn J.D. Chem. Commun. (2005) 1637-1639
19. Stadler M., Anke H., Shan R., and Sterner O. J. Antibiot. 48 (1995) 261-266
20. Shan R., Stadler M., Sterner O., and Anke H. J. Antibiot. 49 (1996) 447-452
21. Koft E.R., and Smith III A.B. J. Am. Chem. Soc. 104 (1982) 2659-2661
22. Smith III A.B., and Huryn D.M. J. Org. Chem. 50 (1985) 1342-1344
23. Trofast J., and Wickberg B. Tetrahedron 33 (1977) 875-879
24. For some selected examples, see:
25. Cossy J., Meyer C., Defosseux M., and Blanchard N. Pure Appl. Chem. 77 (2005) 1131-1137
26. Ashfeld B.L., and Martin S.F. Org. Lett. 7 (2005) 4535-4537
27. Defosseux M., Blanchard N., Meyer C., and Cossy J. J. Org. Chem. 69 (2004) 4626-4647
28. Swain N.A., Brown R.C.D., and Bruton G. J. Org. Chem. 69 (2004) 122-129
29. Okuma K., Tanaka Y., Yoshihira K., Ezaki A., Koda G., Ohta H., Hara K., and Kashimura S. J. Org. Chem. 58 (1993) 5915-5917
30. Lautens M., and Delanghe P.H.M. J. Org. Chem. 58 (1993) 5037-5039
31. Corre M.L., Hercouet A., and Bessieres B. J. Org. Chem. 59 (1994) 5483-5484
32. Shao L.-X., Li Y.-X., and Shi M. Chem.-Eur. J. 13 (2007) 862-869
33. Qi M.-H., Shao L.-X., and Shi M. Synthesis (2007) 3567-3573
34. Wang B.-Y., Huang J.-W., Liu L.-P., and Shi M. Synlett (2005) 421-424
35. Shao L.-X., Qi M.-H., and Shi M. Tetrahedron Lett. 49 (2008) 165-168
36. 000=1392; diffractometer: Rigaku AFC7R; residuals: R; Rw: 0.0485, 0.1136.
37. For reviews, see:
38. Adams D.R., and Bhatnagar S.P. Synthesis (1977) 661-672
39. Arundale E., and Mikeska L.A. Chem. Rev. 51 (1952) 505-555