Synthesis and Iodocyclization of Homoallylic Hydroxylamines

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5623-5626

  Fiumana, Andrea ^a   Lombardo, Marco ^a   Trombini, Claudio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000050053     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970544s     Document Type: Article

References (22)

1. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
2. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
3. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
4. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
5. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
6. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
7. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
8. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
9. Owing to the huge number of references on this topic, we only refer to the most recent papers and to references therein: (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083. (e) Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc. Perkin Trans, 1 1996, 875. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (h) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473. Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
10. (a) Mancini, F.; Piazza, M. G.; Trombini, C. J. Org. Chem. 1991, 56, 4246.
11. (b) Dhavale, D. D.; Gentilucci, L.; Piazza, M. G.; Trombini, C. Liebigs Ann. Chem. 1992, 1289.
12. (a) Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239.
13. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
14. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
15. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450.
16. Merchan, F.; Merino, P.; Rojo, P.; Tejero, T.; Dondoni, A. Tetrahedron: Asymmetry 1996, 7, 667.
17. 2OBn 3-5%.
18. In three different experiments we got untractable reaction mixtures; after thiosulfate quenching, we identified a significant amount of benzaldehyde. We believe that oxidation might convert the starting N-benzyl group into a C-phenyl nitrone, which undergoes hydrolysis to benzaldehyde on aqueous workup.
19. A number of methods for the activation of zinc or for the in situ preparation of active forms of zinc are available; see, for example (a) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925. (b) Erdik, E. Tetrahedron 1987, 43, 2203. For our purposes, activation was simply carried out by heating zinc powder (Janssen) at about 300°C with a heat gun for 5 min under argon.
20. A number of methods for the activation of zinc or for the in situ preparation of active forms of zinc are available; see, for example (a) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925. (b) Erdik, E. Tetrahedron 1987, 43, 2203. For our purposes, activation was simply carried out by heating zinc powder (Janssen) at about 300°C with a heat gun for 5 min under argon.
21. An aliquot of allylic zinc bromide solution was quenched with 1 N HCl, and zinc was titrated by EDTA.
22. All the O-silylated hydroxylamines, contrary to starting hydroxylamines, are easily analyzed by GC-MS and show the characteristic fragment due to the loss of the allylic moiety from the molecular ion.