Remarkable template effect of a Lewis acid receptor in the intramolecular radical cyclization: control of reaction pathway as well as stereochemistry

Author:

Ooi Takashi,Hokke Yasutoshi,Tayama Eiji,Maruoka Keiji

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference16 articles.

1. Reviews: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds; Pergamon: New York, 1986. (b) Pattenden, G. Chem. Soc. Rev.1988, 17, 361. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhock, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 715. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev.1991, 91, 1237. (e) Motherwell, W. B.; Crich, D. Free-Radical Reactions in Organic Synthesis; Academic: London, 1992. (f) Beckwith, A. L. J. Chem. Soc. Rev.1993, 22, 143. (g) Melikyan, G. G. Synthesis1993, 833. (h) Molander, G. A.; Harris, C. R. Chem. Rev.1996, 96, 307. (i) Snider, B. B. Chem. Rev.1996, 96, 339. (j) Zard, S. Z. Angew. Chem., Int. Ed. Engl.1997, 36, 673.

2. For recent application to the total synthesis of natural products; see, for example: Sha, C.-K.; Lee, F.-K.; Chang, C.-J. J. Am. Chem. Soc.1999, 121, 9875.

3. (a) Giese, B. Angew. Chem., Int. Ed. Engl.1989, 28, 969. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res.1991, 24, 296. (c) RajanBabu, T. V. Acc. Chem. Res.1991, 24, 139. (d) Smadja, W. Synlett1994, 1. (e) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996.

4. For a recent excellent review on the use of Lewis acids in radical chemistry, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl.1998, 37, 2562.

5. For other synthetic applications, see: (a) Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc.1994, 116, 4131. (b) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett1994, 519. (c) Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc.1995, 117, 9091. (d) Saito, S.; Yamamoto, H. J. Org. Chem.1996, 61, 2928. (e) Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl.1997, 36, 1183. (f) Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc.1998, 120, 813. (g) Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl.1998, 37, 3039. (h) Saito, S.; Shiozawa, M.; Yamamoto, H. Angew. Chem., Int. Ed. Engl.1999, 38, 1769. (i) Kondo, Y.; Kon-i, K.; Iwasaki, A.; Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. Engl.2000, 39, 414. (j) Saito, S.; Shiozawa, M.; Nagahara, T.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc.2000, 122, 7847.

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