NMR studies of three types of highly coordinated organotin hydrides: Chemo-, regio-, and stereoselective reduction of 2,3-epoxy ketones

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 82-87

  Kawakami, Takayo ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002556299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9512416     Document Type: Article

References (77)

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15. 4e-h (a) Castaing, M. D.; Rahm, A. J. Org. Chem. 1986, 51, 665-683. (b) Pereyre, M.; Godet, J. Y. Tetrahedron Lett. 1970, 51, 3653-3656. (c) Fung, N. Y. M.; Mayo, P.; Schauble, J. H.; Weedon, A. C. J. Org. Chem. 1978, 43, 3977-3979. (d) Neumann, W. P ; Heymann, E. Liebigs Ann. Chem 1965, 683, 11-23. (e) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619-622. (f) Kikukawa, K. ; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881-884. (g) Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetraheron Lett. 1990, 31, 6621-6624. (h) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
16. 4e-h (a) Castaing, M. D.; Rahm, A. J. Org. Chem. 1986, 51, 665-683. (b) Pereyre, M.; Godet, J. Y. Tetrahedron Lett. 1970, 51, 3653-3656. (c) Fung, N. Y. M.; Mayo, P.; Schauble, J. H.; Weedon, A. C. J. Org. Chem. 1978, 43, 3977-3979. (d) Neumann, W. P ; Heymann, E. Liebigs Ann. Chem 1965, 683, 11-23. (e) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619-622. (f) Kikukawa, K. ; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881-884. (g) Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetraheron Lett. 1990, 31, 6621-6624. (h) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
17. 4e-h (a) Castaing, M. D.; Rahm, A. J. Org. Chem. 1986, 51, 665-683. (b) Pereyre, M.; Godet, J. Y. Tetrahedron Lett. 1970, 51, 3653-3656. (c) Fung, N. Y. M.; Mayo, P.; Schauble, J. H.; Weedon, A. C. J. Org. Chem. 1978, 43, 3977-3979. (d) Neumann, W. P ; Heymann, E. Liebigs Ann. Chem 1965, 683, 11-23. (e) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619-622. (f) Kikukawa, K. ; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881-884. (g) Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetraheron Lett. 1990, 31, 6621-6624. (h) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
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21. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
22. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
23. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
24. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
25. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
26. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
27. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
28. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
29. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
30. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
31. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
32. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
33. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
34. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
35. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
36. 6m-p were enhanced by the high coordination. (a) Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144-1146. (b) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J Org. Chem. 1986, 51, 2177-2184. (c) Yano, K.; Amishiro, N.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1991, 64, 2661-2667. (d) Shibata, I.; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1992, 33, 7149-7152. (e) Baba, A.; Yasuda, M.; Yano, K.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (f) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1219-1222. (g) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953-1956. (h) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun 1993, 1067-1068. (i) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859-865. (j) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (k) Yasuda, M.; Kato, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. (l) Yasuda, M.; Oh-hata, T ; Shibata, I.; Baba. A.; Matsuda, H.; Sonoda, N. Bull. Chem. Soc. Jpn. 1995, 68, 1180-1186. (m) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1985, 4, 1329-1333. (n) Shibata, I.; Toyota, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1990, 55, 2487-2489. (o) Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909-6914. (p) Shibata, I ; Mori, Y.; Baba, A ; Matsuda, H. Tetrahedron Lett. 1993, 34, 6567-6570.
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66. See the Experimental Section.
67. 3).
68. No iodohydrin intermediate could be isolated.
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