Catalytic C-H bond activation-asymmetric olefin coupling reaction: The first example of asymmetric Fujiwara-Moritani reaction catalyzed by chiral palladium(II) complexes 1

Chemistry Letters

Volumn , Issue 1, 1999, Pages 55-56

  Mikami, Koichi ^a   Hatano, Manabu ^a   Terada, Masahiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033473876     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.55     Document Type: Article

References (39)

1. Presented at the 74th Annual Meeting of the Chemical Society of Japan, K. Mikami, M. Hatano, and M. Terada, Kyoto, 1998, Abstr., 2D639.
2. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
3. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
4. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
5. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
6. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
7. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
8. Reviews: A. E. Shilov and G. B. Shul'pin, Chem. Rev., 97, 2879 (1997); C. Hall and R. N. Perutz, Chem. Rev., 97, 3125 (1997); J. J. Schneider, Angew. Chem., Int. Ed. Engl., 35, 1068 (1996); B. A. Arndtsen, R. G. Bergman, T. A. Mobley, and T. H. Peterson, Acc. Chem. Res., 28, 154 (1995); R. H. Crabtree, J. Organomet. Chem., 1995, 504; R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 32, 789 (1993); J. A. Davies, P. L. Watson, J. F. Liebman, and A. Greenberg, in "Selective Hydrocarbon Activation," Wiley-VCH, New York (1990).
9. Reviews: K. Mikami and M. Terada, in "Lewis Acid Reagents: A Practical Approach," ed by H. Yamamoto, Oxford University Press, Oxford (1998), Chap. 6, p. 93; K. Mikami, Pure Appl. Chem., 68, 639 (1996); K. Mikami, M. Terada, and T. Nakai, in "Advances in Catalytic Process," ed by M. P. Doyle, JAI Press, London (1995), Vol. 1, p. 123; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, Synlett, 1992, 255.
10. Reviews: K. Mikami and M. Terada, in "Lewis Acid Reagents: A Practical Approach," ed by H. Yamamoto, Oxford University Press, Oxford (1998), Chap. 6, p. 93; K. Mikami, Pure Appl. Chem., 68, 639 (1996); K. Mikami, M. Terada, and T. Nakai, in "Advances in Catalytic Process," ed by M. P. Doyle, JAI Press, London (1995), Vol. 1, p. 123; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, Synlett, 1992, 255.
11. Reviews: K. Mikami and M. Terada, in "Lewis Acid Reagents: A Practical Approach," ed by H. Yamamoto, Oxford University Press, Oxford (1998), Chap. 6, p. 93; K. Mikami, Pure Appl. Chem., 68, 639 (1996); K. Mikami, M. Terada, and T. Nakai, in "Advances in Catalytic Process," ed by M. P. Doyle, JAI Press, London (1995), Vol. 1, p. 123; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, Synlett, 1992, 255.
12. Reviews: K. Mikami and M. Terada, in "Lewis Acid Reagents: A Practical Approach," ed by H. Yamamoto, Oxford University Press, Oxford (1998), Chap. 6, p. 93; K. Mikami, Pure Appl. Chem., 68, 639 (1996); K. Mikami, M. Terada, and T. Nakai, in "Advances in Catalytic Process," ed by M. P. Doyle, JAI Press, London (1995), Vol. 1, p. 123; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, Synlett, 1992, 255.
13. Comprehensive reviews on ene reactions: K. Mikami, in "Advnces in Asymmetric Synthesis," ed by A. Hassner, JAI Press, London (1994), Vol. 1, p. 1; K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); B. B. Snider, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, London (1991), Vol. 2, p. 527 and Vol. 5, p. 1; K. Mikami, M. Terada, M. Shimizu, and T. Nakai, J. Synth. Org. Chem. Jpn., 48, 292 (1990).
14. Comprehensive reviews on ene reactions: K. Mikami, in "Advnces in Asymmetric Synthesis," ed by A. Hassner, JAI Press, London (1994), Vol. 1, p. 1; K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); B. B. Snider, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, London (1991), Vol. 2, p. 527 and Vol. 5, p. 1; K. Mikami, M. Terada, M. Shimizu, and T. Nakai, J. Synth. Org. Chem. Jpn., 48, 292 (1990).
15. Comprehensive reviews on ene reactions: K. Mikami, in "Advnces in Asymmetric Synthesis," ed by A. Hassner, JAI Press, London (1994), Vol. 1, p. 1; K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); B. B. Snider, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, London (1991), Vol. 2, p. 527 and Vol. 5, p. 1; K. Mikami, M. Terada, M. Shimizu, and T. Nakai, J. Synth. Org. Chem. Jpn., 48, 292 (1990).
16. Comprehensive reviews on ene reactions: K. Mikami, in "Advnces in Asymmetric Synthesis," ed by A. Hassner, JAI Press, London (1994), Vol. 1, p. 1; K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); B. B. Snider, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, London (1991), Vol. 2, p. 527 and Vol. 5, p. 1; K. Mikami, M. Terada, M. Shimizu, and T. Nakai, J. Synth. Org. Chem. Jpn., 48, 292 (1990).
17. Comprehensive reviews on ene reactions: K. Mikami, in "Advnces in Asymmetric Synthesis," ed by A. Hassner, JAI Press, London (1994), Vol. 1, p. 1; K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); B. B. Snider, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, London (1991), Vol. 2, p. 527 and Vol. 5, p. 1; K. Mikami, M. Terada, M. Shimizu, and T. Nakai, J. Synth. Org. Chem. Jpn., 48, 292 (1990).
18. Review: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524. For selected references, see: Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); Y. Fuchita, K. Hiraki, Y. Kamogawa, M. Suenaga, K. Tohgoh, and Y. Fujiwara, Bull. Chem. Soc. Jpn., 62, 1081 (1989).
19. Review: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524. For selected references, see: Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); Y. Fuchita, K. Hiraki, Y. Kamogawa, M. Suenaga, K. Tohgoh, and Y. Fujiwara, Bull. Chem. Soc. Jpn., 62, 1081 (1989).
20. Review: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524. For selected references, see: Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); Y. Fuchita, K. Hiraki, Y. Kamogawa, M. Suenaga, K. Tohgoh, and Y. Fujiwara, Bull. Chem. Soc. Jpn., 62, 1081 (1989).
21. For an excellent textbook on palladium chemistry: J. Tsuji, "Palladium Reagents and Catalysts," John Wiley & Sons, Chichester (1995).
22. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
23. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
24. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
25. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
26. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
27. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
28. Pioneering work by Hosokawa-Murahashi: T. Hosokawa, T. Uno, S. Inui, and S. Murahashi, J. Am. Chem. Soc., 103, 2318 (1981). T. Hosokawa and S. Murahashi, Acc. Chem. Res., 23, 49 (1990). Quite recent example on catalytic asymmetric Wacker-type cyclization: Y. Uozumi, K. Kalo, and T. Hayashi, J. Am. Chem. Soc. 119, 5063 (1997). Chiral benzoquinone as a reoxidant: K. Itami, A. Palmgren, A. Thorarensen, and J.-E. Backvall, J. Org. Chem., 63, 6466 (1998). Also see: M. Calter, T. K. Hollis, L. E. Overman, J. Ziller, G. G. Zipp, J. Org. Chem. 62, 1449 (1997); T. K. Hollis and L. E. Overman, Tetrahedron Lett., 38, 8837 (1997); E. Hagiwara, A. Fujii, and M. Sodeoka, J. Am. Chem. Soc., 120, 2474 (1998).
29. Quite recently, Murai et al. reported an asymmetric C-H activation of vinylic C-H bond following intramolecular olefin coupling reaction, namely asymmeric cyclization of 1,5-diene catalyzed by Rh complexes with chiral ferrocene ligands: N. Fujii, F. Kakiuchi, A. Yamada, N. Chatani, and S. Murai, Chem. Lett., 1997, 425.
30. For asymmetric cyclopalladation of dimethylaminomethyl-ferrocene using an equimolar amount of chiral Pd(II) species to dimethylaminomethylferrocene(I) substrate: V. I. Sokolov, L. L. Troitskaya, and O. A. Reutov, J. Organomet. Chem., 182, 537 (1979).
31. For asymmetric zirconacycle formation using an equimolar amount of chiral zirconocene complex: S. Rodewald and R. F. Jordan, J. Am. Chem. Soc., 116, 4491 (1994).
32. For a Ru-catalyzed addition of an aromatic C-H bond to a double bond, see: S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); Pure Appl. Chem., 66, 1527 (1994) and references cited therein. Also see: S. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J. Org. Chem., 55, 1286 (1990); T. Mitsudo, S.-W. Zhang, and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1994, 435.
33. For a Ru-catalyzed addition of an aromatic C-H bond to a double bond, see: S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); Pure Appl. Chem., 66, 1527 (1994) and references cited therein. Also see: S. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J. Org. Chem., 55, 1286 (1990); T. Mitsudo, S.-W. Zhang, and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1994, 435.
34. For a Ru-catalyzed addition of an aromatic C-H bond to a double bond, see: S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); Pure Appl. Chem., 66, 1527 (1994) and references cited therein. Also see: S. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J. Org. Chem., 55, 1286 (1990); T. Mitsudo, S.-W. Zhang, and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1994, 435.
35. For a Ru-catalyzed addition of an aromatic C-H bond to a double bond, see: S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); Pure Appl. Chem., 66, 1527 (1994) and references cited therein. Also see: S. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J. Org. Chem., 55, 1286 (1990); T. Mitsudo, S.-W. Zhang, and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1994, 435.
36. For a Ru-catalyzed addition of an aromatic C-H bond to a double bond, see: S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); Pure Appl. Chem., 66, 1527 (1994) and references cited therein. Also see: S. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J. Org. Chem., 55, 1286 (1990); T. Mitsudo, S.-W. Zhang, and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1994, 435.
37. J. Tsuji and H. Nagashima, Tetrahedron, 40, 2699 (1984).
38. -3. X-Ray diffraction data were collected on a Rigaku AFC7R diffractometer with graphite-monochromated Mo-Kα (λ = 0.71069 Å) at -50 °C and the structure was solved by direct methods (SIR92). All non hydrogen atoms were refined anisotropically. The final cycle of full-matrix least-squares refinement was based on 7358 observed reflections (I > 3σ(I)) and 902 variable parameters and converged to R = 0.030 and Rw = 0.027.
39. C.-L. Fang, H. Suemune, and K. Sakai, J. Org. Chem., 57, 4300 (1992).