Intramolecular Tandem Michael-Type Addition/Aldol Cyclization Induced by TiCl4-R4NX Combinations

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3111-3114

  Yagi, Kazunari ^a   Turitani, Takayuki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

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ARTICLE;

EID: 0001564208     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026413h     Document Type: Article

References (35)

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5. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
6. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
7. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
8. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
9. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
10. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
11. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
12. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
13. For recent examples of aldol and Michael cyclizations, see: (a) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112. (b) Baik, T.-G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (c) Chiu, P.; Szeto, P.-C.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901. (d) Nagaoka, Y.; Tomioka, K. Org. Lett. 1999, 1, 1467. (e) Ono, M.; Nishimura, K.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1999, 40, 6979. (f) Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem. 2001, 66, 8199. (g) Kamenecka, T. M.; Overman, L. E.; Ly Sakata, S. K. Org. Lett. 2002, 4, 79. (h) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 3403. (i) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
14. 4NI and related mixtures in similar reactions, see: (a) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (b) Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854. (c) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (d) Shi, M.; Jiang, J.-K.; Cui, S.-C.; Feng, Y.-S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
15. 4NI and related mixtures in similar reactions, see: (a) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (b) Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854. (c) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (d) Shi, M.; Jiang, J.-K.; Cui, S.-C.; Feng, Y.-S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
16. 4NI and related mixtures in similar reactions, see: (a) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (b) Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854. (c) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (d) Shi, M.; Jiang, J.-K.; Cui, S.-C.; Feng, Y.-S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
17. 4NI and related mixtures in similar reactions, see: (a) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (b) Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854. (c) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (d) Shi, M.; Jiang, J.-K.; Cui, S.-C.; Feng, Y.-S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
18. 4 alone as both a Lewis acid and a halogen source for Michael-type addition/aldol reactions, see: (a) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1. (b) Li, G.; Gao, J., Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Wei, H.-X.; Kim, S. H.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397.
19. 4 alone as both a Lewis acid and a halogen source for Michael-type addition/aldol reactions, see: (a) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1. (b) Li, G.; Gao, J., Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Wei, H.-X.; Kim, S. H.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397.
20. 4 alone as both a Lewis acid and a halogen source for Michael-type addition/aldol reactions, see: (a) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1. (b) Li, G.; Gao, J., Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Wei, H.-X.; Kim, S. H.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397.
21. (a) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4767.
22. (b) Yachi, K.; Maeda, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5161.
23. (c) Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1999, 40, 8121.
24. (d) Tsuritani, T.; Ito, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2000, 65, 5066.
25. (e) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987.
26. (f) Tsuritani, T.; Shinokubo, H.; Oshima, K. Synlett 2002, 978.
27. 13C NMR.
28. 2AlSPh, see: Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 361.
29. 2AlSPh, see: Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 361.
30. For recent examples of Baylis - Hilman cyclization, see: (a) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404. (b) Wang, L. C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402 and references therein.
31. For recent examples of Baylis - Hilman cyclization, see: (a) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404. (b) Wang, L. C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402 and references therein.
32. 4NI combination does not have enough Lewis acidity to activate an acetal.
33. 4. Concentration and purification afforded 7a (214 mg) in 99% yield.
34. Crystal lographic data for the structures reported herein have been deposited with the Cambridge Crystallographic Data Center (CCDC 186739 and 186740 for 2b and 7e, respectively). Copies of this data can be obtained, free of charge, upon application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: 44-1223-3360033. E-mail: deposit@ ccdc.cam.ac.uk.
35. A similar model to account for the stereochemical outcome has been proposed. See ref 2h.