The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes

Tetrahedron

Volumn 52, Issue 10, 1996, Pages 3631-3658

  Binns, Falmai ^a   Hayes, Roy ^a   Hodgetts, Kevin J ^a   Saengchantara, Suthiweth T ^a   Wallace, Timothy W ^a   Wallis, Christopher J ^b  

^a UNIVERSITY OF SALFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 OXABICYCLO[3.2.0]HEPTANE DERIVATIVE; ALDEHYDE; ALKADIENE; BICYCLO[3.2.0]HEPTANE DERIVATIVE; CYCLOBUTANE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030069041     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00039-7     Document Type: Article

References (56)

1. On leave from the Chemistry Division, Department of Science Service, Rama 6 Road, Phayatai, Bangkok 10400, Thailand.
2. Woodward, R.B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
3. Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S.T.; Turner, R.W.; Wallace, T.W. Tetrahedron 1992, 48, 515.
4. Rudolf, K.; Spellmeyer, D.C.; Houk, K.N. J. Org. Chem. 1987, 52, 3708.
5. For related work, see (a) Rondan, N.G.; Houk, K.N. J. Am. Chem. Soc. 1985, 107, 2099;
6. (b) Buda, A.B.; Wang, Y.; Houk, K.N. J. Org. Chem. 1989, 54, 2264;
7. (c) Piers, E.; Lu, Y.-F. J. Org. Chem. 1989, 54, 2267;
8. (d) Niwayama, S.; Houk, K.N. Tetrahedron Lett. 1992, 33, 883;
9. (e) Niwayama, S.; Houk, K.N. Tetrahedron Lett. 1993, 34, 1251;
10. (f) Piers, E.; Ellis, K.A. Tetrahedron Lett. 1993, 34, 1875;
11. (g) Niwayama, S.; Wang, Y.; Houk, K.N. Tetrahedron Lett. 1995, 36, 6201.
12. Ingham, S.; Turner, R.W.; Wallace, T.W. J. Chem. Soc., Chem. Commun. 1985, 1664.
13. For preliminary accounts of this work, see (a) Hodgetts, K.J.; Saengchantara, S.T.; Wallis, C.J.; Wallace, T.W. Tetrahedron Lett. 1993, 34, 6321;
14. (b) Hodgetts, K.J.; Wallis, C.J.; Wallace, T.W. Tetrahedron Lett. 1994, 35, 4645;
15. (c) Hodgetts, K.J.; Wallis, C.J.; Wallace, T.W. Synlett 1995, 1235.
16. Posner, G.H.; Ting, J.-S. Tetrahedron Lett. 1974, 683; Posner, G.H.; Ting, J.-S.; Lentz, C.M. Tetrahedron 1976, 32, 2281. See also Fernández Mateos, A.; Pascual Coca, G.; Pérez Alonso, J.J.; Rubio Gonzalez, R.; Tapia Hernández, C. Tetrahedron Lett. 1995, 36, 621, and references cited therein.
17. Posner, G.H.; Ting, J.-S. Tetrahedron Lett. 1974, 683; Posner, G.H.; Ting, J.-S.; Lentz, C.M. Tetrahedron 1976, 32, 2281. See also Fernández Mateos, A.; Pascual Coca, G.; Pérez Alonso, J.J.; Rubio Gonzalez, R.; Tapia Hernández, C. Tetrahedron Lett. 1995, 36, 621, and references cited therein.
18. Posner, G.H.; Ting, J.-S. Tetrahedron Lett. 1974, 683; Posner, G.H.; Ting, J.-S.; Lentz, C.M. Tetrahedron 1976, 32, 2281. See also Fernández Mateos, A.; Pascual Coca, G.; Pérez Alonso, J.J.; Rubio Gonzalez, R.; Tapia Hernández, C. Tetrahedron Lett. 1995, 36, 621, and references cited therein.
19. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
20. 1H n.m.r. spectra). (2Z,4E)-Dienals [δ ca, 10.2 ppm, CHO] were the only (Z,E)-isomers detected in the ring-opened products. Isomerisation to the more stable (2E,4E)-isomers [δ ca. 9.5 ppm, CHO], which is catalysed by acid, appeared to be the only source of contamination. The (2Z,4E)-dienals were used without delay.
21. Müller, D.G.; Jaenicke, L. FEBS Lett. 1973, 30, 137.
22. 13C), and by comparison with published data.
23. Chrétien-Bessière, Y.; Garnero, J.; Benezet, L.; Peyron, L. Bull. Soc. Chim. Fr. 1967, 97; Naves, Y.-R. Bull Soc. Chim. Fr. 1967, 3152.
24. Chrétien-Bessière, Y.; Garnero, J.; Benezet, L.; Peyron, L. Bull. Soc. Chim. Fr. 1967, 97; Naves, Y.-R. Bull Soc. Chim. Fr. 1967, 3152.
25. Moore, R.E.; Pettus, J.A.; Mistysyn, J. J. Org. Chem. 1974, 39, 2201, and references cited therein.
26. For recent syntheses and a bibliography, see Chapuis, C. Tetrahedron Lett. 1992, 33, 2461; Fehr, C.; Galindo, J.; Chappuis, S. Tetrahedron Lett. 1992, 33, 2465.
27. For recent syntheses and a bibliography, see Chapuis, C. Tetrahedron Lett. 1992, 33, 2461; Fehr, C.; Galindo, J.; Chappuis, S. Tetrahedron Lett. 1992, 33, 2465.
28. Corey, E.J.; Gillman, H.W.; Ganem, B.E. J. Am. Chem. Soc. 1968, 90, 5616.
29. For other syntheses of 17, see (a) Baeckström, P.; Jacobsson, U.; Norin, T.; Unelius, C.R. Tetrahedron 1988, 44, 2541;
30. (b) Stille, J.K.; Groh, B.L. J. Am. Chem. Soc. 1987, 109, 813.
31. Crombie, L. J. Chem. Soc. 1955, 1007, and references cited therein.
32. Heinz, D.E.; Jennings, W.G. J. Food Sci. 1966, 31, 69 (Chem. Abs. 1966, 64, 11769f).
33. Heinz, D.E.; Jennings, W.G. J. Food Sci. 1966, 31, 69 (Chem. Abs. 1966, 64, 11769f).
34. For discussions, see Underiner, T.L.; Goering, H.L. J. Org. Chem. 1990, 55, 2757; Nakanishi, N.; Matsubara, S.; Utimoto, K.; Kozima, S.; Yamaguchi, R. J. Org. Chem. 1991, 56, 3278.
35. For discussions, see Underiner, T.L.; Goering, H.L. J. Org. Chem. 1990, 55, 2757; Nakanishi, N.; Matsubara, S.; Utimoto, K.; Kozima, S.; Yamaguchi, R. J. Org. Chem. 1991, 56, 3278.
36. McDougal, P.G.; Rico, J.G.; Oh, Y.-I.; Condon, B.D. J. Org. Chem. 1986, 51, 3388.
37. Quimpère, M.; Ruest, L.; Deslongchamps, P. Synthesis 1992, 132.
38. Ley, S.V.; Norman, J.; Griffith, W.P.; Marsden, S.P. Synthesis 1994, 639, and references cited therein.
39. All compounds are racemic. Yields refer to isolated, chromatographically homogeneous materials.
40. Clauss, K. Justus Liebigs Ann. Chem. 1968, 777, 19. The reagent was prepared in THF/hexane.
41. Bloch, R.; Brillet, C. Synlett 1991, 829.
42. For a review and leading references, see Huryn, D.M. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991; Vol. 1, p 49. For a close analogy, see Bloch, R.; Gilbert, L. Tetrahedron Lett. 1987, 28, 423.
43. For a review and leading references, see Huryn, D.M. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991; Vol. 1, p 49. For a close analogy, see Bloch, R.; Gilbert, L. Tetrahedron Lett. 1987, 28, 423.
44. Anh, N.T. Topics Curr. Chem. 1980, 88, 145; Houk, K.N.; Paddon-Row, M.N.; Rondan, N.G.; Wu, Y.; Brown, F.K.; Spellmeyer, D.C.; Metz, J.T.; Li, Y.; Loncharich, R.J. Science 1986, 237, 1108.
45. Anh, N.T. Topics Curr. Chem. 1980, 88, 145; Houk, K.N.; Paddon-Row, M.N.; Rondan, N.G.; Wu, Y.; Brown, F.K.; Spellmeyer, D.C.; Metz, J.T.; Li, Y.; Loncharich, R.J. Science 1986, 237, 1108.
46. Perspective views of the cyclobutene moiety were generated using the published X-ray crystal data for cis-3-cyclobutene-1,2-dicarboxylic acid (Benedetti, E.; Ciajolo, M.R.; Declercq, J.P.; Germain, G. Acta Cryst. 1974, B30, 2873).
47. Saksena, A.K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273.
48. Labelle, M.; Falgueyret, J.-P.; Riendeau, D.; Rokach, J. Tetrahedron 1990, 46, 6301.
49. Kosugi, H.; Sekiguchi, S.; Sekita, R.; Uda, H. Bull. Chem. Soc. Jpn. 1976, 49, 520.
50. Harvey, I.; Crout, D.H.G. Tetrahedron: Asymmetry 1993, 4, 807.
51. Lukas, K.-L. German patent DE 36 13312 A1 (1987).
52. Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589.
53. For a pertinent review, see Faber, K.; Riva, S. Synthesis 1992, 895.
54. Perrin, D.D.; Armarego, W.L.F.; Perrin, D.R. Purification of Laboratory Chemicals; 2nd edition; Pergamon: Oxford, 1980.
55. Still, W.C.; Khan, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
56. Nakata, T.; Tani, Y.; Hatozaki, M.; Oishi, T. Chem. Pharm. Bull. 1984, 32, 1411.