First synthesis and stereochemistry of enantiomerically pure spiroselenurane and spirotellurane using the 2-exo-hydroxy-10-bornyl group as a chiral ligand

Author:

Zhang Jian,Takahashi Shigemasa,Saito Shinichi,Koizumi Toru

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference47 articles.

1. Recent reviews on reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164–185. (b) Tidwell, T. T. Synthesis 1990, 857–870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202–208. (d) Kita, Y. Phosphorus, Sulfur and Silicon 1997, 120 and 121, 145–164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600–608. Recent examples involving the formation of chalcogenuranes as the intermediates: (f) Ohkata, K.; Ohnishi, M.; Yoshinaga, K.; Akiba, K.; Rongione, J. C.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 9270–9276. (g) Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1995, 117 6388–6389. (h) Ruano, J. L. G.; Castro, A. M. M.; Ramso, J. H. R. Tetrahedron Lett. 1996, 37, 4569–4572. (i) Jeske, J.; du Mont, W.-W.; Jones, P. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2653–2655. (j) Minoura, M.; Sagami, T.; Akiba, K.; Modrakowski, C.; Sudau, A.; Seppelt, K.; Wallenhauer, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2660–2662. (k) Ruano, J. L. G.; Castro, A. M. M.; Ramso, J. H. R.; Flamarique, A. C. R. Tetrahedron: Asymmetry 1997, 8, 3503–3511. (l) Ramsden, C. A.; Smith, R. G. J. Am. Chem. Soc. 1998, 120, 6842–6843, and references cited therein.

2. On the chemistry of chalcogenuranes: (a) Martin, J. C.; Paul, I. C. Science 1976, 191, 154–159. (b) Oae, S. Organic Chemistry of Sulfur; Kagakudoujin: Kyoto, 1982; chapter 8. (c) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F.; Csizmadia, I. G.; Mangini, A., Eds; Elsevier: Amsterdam, 1985; pp. 408–483. (d) Martin, J. C. Science 1983, 221, 509–514. (e) Furukawa, N.; Sato, S. In Chemistry of Hypervalent Organic Compounds, Preparation and Reactivity of the Hypervalent Chalcogen Compounds; KIKAN KAGAKU SOSETSU, 1998, 34, 41–56, Japanese Chemistry Society, Tokyo, 1998.

3. (a) Kapovits, I.; Kálmán, A. J. Chem. Soc., Chem. Commun. 1971, 649–650.

4. (j) Ádám, T.; Ruff, F.; Kapovits, I.; Szabó, D.; Kucsman, Á. J. Chem. Soc., Perkin Trans. 2 1998, 1269–1275.

5. (b) Adzima, L. J.; Martin, J. C. J. Org. Chem. 1977, 42, 4006–4016.

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