Inter- and intramolecular [2+2]-photocycloaddition of tetronates - Stereoselectivity, mechanism, scope and synthetic applications

European Journal of Organic Chemistry

Volumn , Issue 22, 2004, Pages 4582-4595

  Kemmler, Michael ^a   Herdtweck, Eberhardt ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cycloadditions; Diastereoselectivity; Lactone; Oxygen heterocycles; Photochemistry

Indexed keywords

3 METHYL 4 (2 VINYLCYCLOPENTANYLOXY)FURAN 2(5H) ONE; 3 TERT BUTYL 4 (2 VINYLCYCLOPENTANYLOXY)FURAN 2(5H) ONE; 4 (2 METHOXYETHOXYMETHOXY)FURAN 2(5H) ONE; 4 (2 VINYLCYCLOPENTANYLOXY)FURAN 2(5H) ONE; 4 (3 METHYLBUT 3 ENYLOXY)FURAN 2(5H) ONE; 4 (3,4 DIMETHYLPENT 3 ENYLOXY)FURAN 2(5H) ONE; 4 (4 ETHOXYPENTYLOXY)FURAN 2(5H) ONE; 4 (4 METHYLPENT 3 ENYLOXY)FURAN 2(5H) ONE; 4 (BUT 3 ENYLOXY) 3 METHYLFURAN 2(5H) ONE; 4 (BUT 3 ENYLOXY) 5 METHYLFURAN 2(5H) ONE; 4 (HEX 5 ENYLOXY)FURAN 2(5H) ONE; 4 (PENT 4 ENYLOXY)FURAN 2(5H) ONE; 4 METHOXY 3 (PENT 4 ENYL)FURAN 2(5H) ONE; 5 (BUT 3 ENYL) 4 METHOXYFURAN 2(5H) ONE; ACETONE; ALCOHOL; ALKENYL GROUP; ALKYL BROMIDE; BROMINE DERIVATIVE; CARBON; CHEMICAL COMPOUND; CYCLOPENTENE DERIVATIVE; ETHER; HYDROXYL GROUP; OXEPANE DERIVATIVE; PIPERYLENE; SOLVENT; TERT BUTYL ALCOHOL; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; ARTICLE; ATOM; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; IRRADIATION; MECHANICS; MITSUNOBU REACTION; MOLECULE; PHOTOCYCLOADDITION; PRECURSOR; PROTECTION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 12444344831     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400551     Document Type: Article

References (63)

1. [1a] S. L. Schreiber, Science 1985, 227, 857-863.
2. [1b] S. A. Fleming, C. L. Bradford, J. J. Gao, in: Molecular and Supramolecular Photochemistry, Organic Photochemistry, 1 (Ed.: K. S. S. V. Ramamurthy), Marcel Dekker, New York, 1997, 186-243.
3. [1c]T. Bach, Synthesis 1998, 683-703.
4. [1d] J.-P. Pete, in: CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Ed.: F. Lenci, W. M. Horspool), CRC Press, New York, 2004, 71.1-71.14.
5. [2a] P. A. Wender, in: Photochemistry in Organic Synthesis (Ed.: J. D. Coyle), Royal Society of Chemistry, London, 1986, 163-188.
6. [2b]M. Demuth, G. Mikhail, Synthesis 1989, 145-161.
7. [2c] D. De Keukeleire, S.-L. He, Chem. Rev. 1993, 93, 359-380.
8. [2d] B. Grosch, T. Bach, in: CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Eds.: F. Lenci, W. M. Horspool), CRC Press, New York, 2004, 61.1-61.14.
9. [3a] M. T. Crimmins, Chem. Rev. 1988, 88, 1453-1473.
10. [3b] M. T. Crimmins, T. E. Reinhold, Org. React. 1993, 44, 297-588.
11. D. I. Schuster, in: CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Eds.: F. Lenci, W. M. Horspool), CRC Press, New York, 2004, 72.1-72.24.
12. [5a] S. Ghosh, S. R. Raychaudhury, R. G. Salomon, J. Org. Chem. 1987, 52, 83-90.
13. [5b] S. Ghosh, in Handbook of Photochemistry and Photobiology, 2nd ed. (Eds.: F. Lenci, W. M. Horspool), CRC Press, New York, 2004, 18.1-18.19.
14. M. Kemmler, T. Bach, Angew. Chem. Int. Ed. 2003, 42, 4824-4826; Angew. Chem. 2003, 115, 4973-4975.
15. M. Kemmler, T. Bach, Angew. Chem. Int. Ed. 2003, 42, 4824-4826; Angew. Chem. 2003, 115, 4973-4975.
16. P. G. Bauslaugh, Synthesis 1970, 287-300.
17. H. Kosugi, S. Segiguchi, R.-I. Sekita, H. Uda, Bull. Chem. Soc., Jpn. 1976, 49, 520-528.
18. F. W. Curtius, H.-D. Scharf, Tetrahedron: Asymmetry 1996, 7, 2957-2961.
19. [10a] S. Gelin, P. Pollet, Synth. Commun. 1980, 10, 805-811.
20. [10b] T. Momose, N. Toyooka, H. Fujii, H. Yanagino, Heterocycles 1989, 29, 453-458.
21. [10c] J. W. J. F. Thuring, A. A. M. A. V. Gaal, S. J. Hornes, M. M. D. Kok, G. H. L. Nefkens, B. Zwanenburg, J. Chem. Soc., Perkin Trans. 1 1997, 767-774.
22. [10d] W. Zhang, Tetrahedron Lett. 2000, 41, 2523-2527.
23. [10e] T. Mukaiyama, T. Shintou, K. Fukumoto, J. Am. Chem. Soc. 2003, 125, 10538-10539.
24. [10f] F. F. Paintner, L. Allmendinger, G. Bauschke, Synlett 2003, 83-86.
25. H. Martin, R. Hoffmann, B. Schmidt, S. Wolff, Tetrahedron 1989, 45, 6113-6126.
26. J. S. Bajwa, R. C. Anderson, Tetrahedron Lett. 1990, 31, 6973-6976.
27. T. Sato, K. Yoshimatsu, J. Otera, Synlett 1995, 843-846.
28. W. D. Kumler, J. Am. Chem. Soc. 1938, 60, 859-864.
29. H. Wyss, U. Voegeli, R. Scheffold, Helv. Chim. Acta 1981, 64, 775-786.
30. H. Zimmer, A. Amer, C. Van Pham, D. Grob-Schmidt, J. Org. Chem. 1988, 53, 3368-3370.
31. S. Brandaenge, L. Flodman, A. Norberg, J. Org. Chem. 1984, 49, 927-928.
32. L. W. Rotherham, J. E. Semple, J. Org. Chem. 1998, 63, 6667-6672.
33. J. D. White, T. Nishiguchi, R. W. Skeean, J. Am. Chem. Soc. 1982, 104, 3923-3928.
34. J. A. Macritchie, A. Silcock, C. L. Willis, Tetrahedron: Asymmetry 1997, 8, 3895-3902.
35. [21a] A. R. Matlin, C. F. Albert, S. Wolff, W. C. Agosta, J. Am. Chem. Soc. 1986, 108, 3385-3394.
36. [21b] M. T. Crimmins, P. S. Watson, Tetrahedron Lett. 1993, 34, 199-202.
37. [22a] T. W. Flechtner, J. Org. Chem. 1977, 42, 901-903.
38. [22b] E. Anklam, P. Margaretha, Helv. Chim. Acta 1983, 66, 1466-1474.
39. [22c] A. Naim, G. Mills, P. B. Shevlin, Tetrahedron Lett. 1992, 33, 6779-6782.
40. [23a] J. R. Anderson, R. L. Edwards, A. A. Freer, R. P. Mabelis, J. P. Poyser, H. Spencer, A. J. S. Whalley, J. Chem. Soc., Chem. Commun. 1984, 917-919.
41. [23b] J. R. Anderson, R. L. Edwards, J. P. Poyser, A. J. S. Whalley, J. Chem. Soc., Perkin Trans. 1 1988, 823-831.
42. [24a] S. W. Baldwin, T. J. Mazzuckelli, Tetrahedron Lett. 1986, 27, 5975-5978.
43. [24b] R. Alibes, J. L. Bourdelande, J. Font, A. Gregori, T. Parella, Tetrahedron 1996, 52, 1267-1278.
44. [24c] A. Gregori, R. Alibes, J. L. Bourdelande, J. Font, Tetrahedron Lett. 1998, 39, 6961-6962.
45. K. Tomioka, K. K. M. Tanaka, Tetrahedron Lett. 1982, 23, 3401-3404.
46. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
47. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
48. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
49. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
50. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
51. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
52. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
53. -3). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC-239366 (33a) and CCDC-239365 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. Data Collection Software for NONIUS DIP devices, Delft (The Netherlands), 1997; L. Straver, Enraf-Nonius CAD4 Operating System Version 5.0. B.V. Enraf-Nonius, Delft, The Netherlands, 1989; C.K. Fair, MoleN An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990. Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435-436; International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson)
54. [27a] R. A. Caldwell, W. Tang, D. I. Schuster, G. E. Heibel, Photochem. Photobiolog. 1991, 53, 159-164.
55. [27b] D. I. Schuster, D. A. Dunn, G. E. Heibel, P. B. Brown, J. M. Rao, J. Woning, R. Bonneau, J. Am. Chem. Soc. 1991, 113, 6245-6255.
56. [27c] N. A. Kaprinidis, G. Lem, S. H. Courtney, D. I. Schuster, J. Am. Chem. Soc. 1993, 115, 3324-3325.
57. M. W. Schmidt, E. K. C. Lee, J. Am. Chem. Soc. 1970, 92, 3579-3586.
58. [29a] P. De Mayo, H. Takeshita, Can. J. Chem. 1963, 41, 440-449.
59. [29b] P. De Mayo, Acc. Chem. Res. 1971, 4, 41-48.
60. T Bach, S. Heuser, Chem. Eur. J. 2002, 8, 5585-5592.
61. A. N. De Silva, C. L. Francis, A. D. Ward, Aust. J. Chem. 1993, 46, 1657-1671.
62. R. W. Hoffmann, G. Niel, Liebigs Ann. Chem. 1991, 1195-1201.
63. L. A. Arnold, R. Naasz, A. J. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254.