Enantioselective intramolecular [2+2]-photocycloaddition reactions in solution

Angewandte Chemie - International Edition

Volumn 39, Issue 13, 2000, Pages 2302-2304

  Bach, Thorsten ^a,b   Bergmann, Hermann ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Asymmetric synthesis; Cycloadditions; Host guest chemistry; Lactams; Photochemistry

Indexed keywords

ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034601015     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000703)39:13<2302::AID-ANIE2302>3.0.CO;2-6     Document Type: Article

References (31)

1. Reviews: a) S. R. L. Everitt, Y. Inoue in Molecular and Supramolecular Photochemistry: Organic Molecular Photochemistry, Vol. 3 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1999. pp. 71-130; b) Y. Inoue, Chem. Rev. 1992, 92, 741-770; c) H. Rau, Chem. Rev. 1983, 83, 535-547.
2. Reviews: a) S. R. L. Everitt, Y. Inoue in Molecular and Supramolecular Photochemistry: Organic Molecular Photochemistry, Vol. 3 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1999. pp. 71-130; b) Y. Inoue, Chem. Rev. 1992, 92, 741-770; c) H. Rau, Chem. Rev. 1983, 83, 535-547.
3. Reviews: a) S. R. L. Everitt, Y. Inoue in Molecular and Supramolecular Photochemistry: Organic Molecular Photochemistry, Vol. 3 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1999. pp. 71-130; b) Y. Inoue, Chem. Rev. 1992, 92, 741-770; c) H. Rau, Chem. Rev. 1983, 83, 535-547.
4. Reviews on auxiliary-controlled stereoselective photochemical reactions: a) T. Bach, Synthesis 1998, 683-703; b) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1997. pp. 187-243; c) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216; d) J. Mattay, R. Conrads, R. Hoffmann, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E 21c. 1995, pp. 3085-3178; e) M. Demuth, G. Mikhail. Synthesis 1989. 145-162.
5. Reviews on auxiliary-controlled stereoselective photochemical reactions: a) T. Bach, Synthesis 1998, 683-703; b) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1997. pp. 187-243; c) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216; d) J. Mattay, R. Conrads, R. Hoffmann, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E 21c. 1995, pp. 3085-3178; e) M. Demuth, G. Mikhail. Synthesis 1989. 145-162.
6. Reviews on auxiliary-controlled stereoselective photochemical reactions: a) T. Bach, Synthesis 1998, 683-703; b) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1997. pp. 187-243; c) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216; d) J. Mattay, R. Conrads, R. Hoffmann, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E 21c. 1995, pp. 3085-3178; e) M. Demuth, G. Mikhail. Synthesis 1989. 145-162.
7. Reviews on auxiliary-controlled stereoselective photochemical reactions: a) T. Bach, Synthesis 1998, 683-703; b) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1997. pp. 187-243; c) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216; d) J. Mattay, R. Conrads, R. Hoffmann, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E 21c. 1995, pp. 3085-3178; e) M. Demuth, G. Mikhail. Synthesis 1989. 145-162.
8. Reviews on auxiliary-controlled stereoselective photochemical reactions: a) T. Bach, Synthesis 1998, 683-703; b) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Marcel Dekker, New York, 1997. pp. 187-243; c) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216; d) J. Mattay, R. Conrads, R. Hoffmann, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. F. 21c. 1995, pp. 3085-3178; e) M. Demuth, G. Mikhail. Synthesis 1989. 145-162.
9. Some selected examples from the field of [2 t 2]-photocycloaddition chemistry: a) L. M. Tolbert, M. B. Ali. J. Am. Chem. Soc. 1982, 104. 1742-1744; b) H. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217-3220: c) A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307; d) M. Demuth, A. Palomer, H.-D. Sluma. A. K. Dey.C. Krüger. Y.-H. Tsay, Angew. Chem. 1986, 98, 1093-1095: Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119.
10. Some selected examples from the field of [2 t 2]-photocycloaddition chemistry: a) L. M. Tolbert, M. B. Ali. J. Am. Chem. Soc. 1982, 104. 1742-1744; b) H. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217-3220: c) A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307; d) M. Demuth, A. Palomer, H.-D. Sluma. A. K. Dey.C. Krüger. Y.-H. Tsay, Angew. Chem. 1986, 98, 1093-1095: Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119.
11. Some selected examples from the field of [2 t 2]-photocycloaddition chemistry: a) L. M. Tolbert, M. B. Ali. J. Am. Chem. Soc. 1982, 104. 1742-1744; b) H. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217-3220: c) A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307; d) M. Demuth, A. Palomer, H.-D. Sluma. A. K. Dey.C. Krüger. Y.-H. Tsay, Angew. Chem. 1986, 98, 1093-1095: Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119.
12. Some selected examples from the field of [2 t 2]-photocycloaddition chemistry: a) L. M. Tolbert, M. B. Ali. J. Am. Chem. Soc. 1982, 104. 1742-1744; b) H. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217-3220: c) A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307; d) M. Demuth, A. Palomer, H.-D. Sluma. A. K. Dey.C. Krüger. Y.-H. Tsay, Angew. Chem. 1986, 98, 1093-1095: Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119.
13. Some selected examples from the field of [2 t 2]-photocycloaddition chemistry: a) L. M. Tolbert, M. B. Ali. J. Am. Chem. Soc. 1982, 104. 1742-1744; b) H. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217-3220: c) A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306-307; d) M. Demuth, A. Palomer, H.-D. Sluma. A. K. Dey.C. Krüger. Y.-H. Tsay, Angew. Chem. 1986, 98, 1093-1095: Angew. Chem. Int. Ed. Engl. 1986, 25, 1117-1119.
14. Photopinacolization: a) D. Seebach, H.-A. Oei, H. Daum. Chem. Ber. 1977, 110, 2316-2333; b) L. Horner, J. Klaus, Liebigs Ann. Chem. 1979, 1232-1257.
15. Photopinacolization: a) D. Seebach, H.-A. Oei, H. Daum. Chem. Ber. 1977, 110, 2316-2333; b) L. Horner, J. Klaus, Liebigs Ann. Chem. 1979, 1232-1257.
16. Photocyclization: T. Naito, Y. Tada, I. Ninomiya, Heterocycles 1984, 22, 237-240.
17. Photochemical rearrangement: D. R. Boyd, R. M. Camphell, J. Grimshaw, D. C. Neill, W. B. Jennings, J. Chem. Soc. Perkin Trans. 1 1985, 849-855.
18. Photodestruction: N. Levi-Minzi, M. Zandomenegni, J. Am. Chem. Soc. 1992, 114, 9300-9304.
19. Photooxygenation: a) L. Weber, I. Imiolcxyk, G. Haufe, D. Rehorek, H. Hennig, J. Chem. Soc. Chem. Commun. 1992, 301-303; b) A. Sakai, H. Tani, T. Aoyama, T. Shioiri, Synlett 1998, 257-258, and references therein.
20. Photooxygenation: a) L. Weber, I. Imiolcxyk, G. Haufe, D. Rehorek, H. Hennig, J. Chem. Soc. Chem. Commun. 1992, 301-303; b) A. Sakai, H. Tani, T. Aoyama, T. Shioiri, Synlett 1998, 257-258, and references therein.
21. Reviews: a) F. Toda, Acc. Chem. Res. 1995, 28, 480-486; b) Y. Ito, Synthesis 1998, 1-32.
22. Reviews: a) F. Toda, Acc. Chem. Res. 1995, 28, 480-486; b) Y. Ito, Synthesis 1998, 1-32.
23. A. Joy, S. Uppili, M. R. Netherton, J. R. Scheffer, V. Ramamurthy, J. Am. Chem. Soc. 2000, 122, 728-729, and references therein.
24. T. Bach, H. Bergmann, K. Harms, J. Am. Chem. Soc. 1999, 121, 10650-10651.
25. C. Kaneko, T. Suzuki, M. Sato, T. Naito, Chem. Pharm. Bull. 1987, 35, 112-123.
26. J. G. Stack, D. P. Curran, S. V. Geib, J. Rebek, Jr., P. Ballester, J. Am. Chem. Soc. 1992, 114, 7007-7018.
27. M. Kajino, Y. Shibouta, K. Nishikawa, K. Meguro, Chem. Pharm. Bull. 1991, 39, 2896-2905.
28. 3) and by the absolute configuration of the irradiation product 2.
29. The reactions were conducted at the indicated temperature with toluene as the solvent (0.15 M solution of 1). Further details regarding the irradiation procedure can be found in: T. Bach, J. Schröder, J. Org. Chem. 1999, 64, 1265-1273. The ee values (ee = |(-)-2-(+)-2)|/[( )-2+(+)-2]) were determined by HPLC analysis (column: Chiracel OD; eluent: hexane/2-propanol, 92/8) of the crude product mixture. The separation of host and product is possible by flash chromatography (pentane/tert-butylmethylether, 1/2). Both enantiomers of the host 5 were employed. Naturally, the direction of the face discrimination changes if (+)-5 is replaced by (-)-5.
30. 3, direct methods, carbon-bound hydrogen atoms calculated, N H atom refined. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Cristallographic Data Centre as supplementary publication no. CCDC-142268. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1E7, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
31. T. Bach, H. Bergmann, K. Harms, unpublished results.