Synthesis of trideca-O-methyl-α-pedunculagin. Diastereo-favoritism studies on intramolecular ester-cyclization of axially chiral diphenic acids with carbohydrate core

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3700-3705

  Itoh, Toshiyuki ^a   Chika, Jun Ichi ^a   Shirakami, Shohei ^a   Ito, Hideyuki ^a   Yoshida, Takashi ^a   Kubo, Yuki ^b   Uenishi, Jun Ichi ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000108639     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950969j     Document Type: Article

References (47)

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2. (b) Okuda, T.; Yoshida, T.; Hatano, T. Phytochemistry 1993, 32, 507, and references cited therein.
3. (a) Ogata, T.; Kato, A. Jpn. Kokai Tokkyo Koho, JP 04264026 A2 920918; Chem. Abstr. 1992, 118, 45735.
4. (b) Kashiwada, Y.; Nonaka, G.; Nishioka, I.; Chang, J.-J.; Lee, K.-H. J. Nat. Prod. 1992, 55, 1033.
5. (c) Kashiwada, Y.; Nonaka, G.; Nishioka, I.; Lee, K. J. H.; Bori, I.; Fukushima, Y.; Bastow, K. F.; Lee, K.-H. J. Pharm. Sci. 1993, 82, 487.
6. (d) Miyamoto, K.; Nomura, M.; Murayama, T.; Furukawa, T.; Hatano, T.; Yoshida, T.; Koshiura, R.; Okuda, T. Biol. Pharm. Bull. 1993, 16(4), 379.
7. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
8. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
9. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
10. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
11. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
12. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
13. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
14. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
15. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
16. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
17. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
18. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
19. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
20. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
21. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
22. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
23. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
24. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
25. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
26. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
27. Because of their interesting properties of pharmacological activity and as catalysts for asymmetric syntheses, efforts toward the development of a simple synthetic means for axially chiral biaryls have greatly increased. For recent examples see: (a) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (b) Jung, M. E.; Kim, C.; Bussche, L. J. Org. Chem. 1994, 59, 3248. (c) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (d) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989, 6993. (e) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732. (g) Hattori, T.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (h) Rama Rao, A. V.; Reddy, K. L.; Reddy, M. M. Ibid. 1994, 35, 5039. (i) Rawal, V. H.; Florjancic, A. S.; Singh, S. P. Ibid. 1994, 35, 8985. (j) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426. (k) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (l) Itoh, T.; Chika, J.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1993, 58, 5717. (m) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242. (n) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748. (o) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (p) Lin, G.; Liu, S.-H.; Chen, S.-J.; Wu, F.-C.; Sun, H.-L. Tetrahedron Lett. 1993, 34, 6057. (q) Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309. (r) Insole, J. M. J. Chem. Res. (M) 1990, 2828. (s) Harada, T.; Oku, A. Synlett 1995, 283. For leading references for both the synthesis and natural occurrence of biaryls see. (t) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977, and references cited therein.
28. This concept can be applied to optical resolution of axially chiral biaryls; Itoh, T.; Chika, J. J. Org. Chem. 1995, 60, 4968.
29. (a) Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742. For preliminary results, see: Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1993, 115, 1162.
30. (a) Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742. For preliminary results, see: Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1993, 115, 1162.
31. (b) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357.
32. (c) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2577.
33. (d) Lipshutz, B. H.; Liu, Z.-P.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567.
34. (a) Schmidt, O. T.; Würtele, L.; Harréus, A. Liebigs, Ann. Chem. 1965, 690, 150.
35. (b) Okuda, T.; Yoshida, T.; Ashida, M.; Yazaki, K. J. Chem. Soc. Perkin Trans. 1 1983, 1765.
36. Tanaka, T.; Kirihara, S.; Nonaka, G-i.; Nishioka, I. Chem. Pharm. Bull. 1993, 41, 1708.
37. (a) Schmidt, O. T. Fortschr. Chem. Org. Naturst. 1956, 13, 70.
38. (b) Haslam, E. Fortschr. Chem. Org. Naturs. 1982, 41, 1.
39. Haslam, E. In Plant Polyphenols; Hemingway, R. W.; Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 169-195. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357.
40. Haslam, E. In Plant Polyphenols; Hemingway, R. W.; Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 169-195. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357.
41. The (R) and (S) nomenclature used prior to the compound refers to the absolute stereochemistry of the chiral axis of the biaryl unit.
42. The ratio was determined by HPLC analysis. No isomer was detected in the reaction in which the best regioselectivity was recorded. Diastereoisomers of (R)-5 and (S)-5 can be isolated using silica gel TLC; we obtained (R)-5 and (S)-5 in a separate run under the same reaction conditions in which the ratio was calculated as 1520:1. Based on this result, the ratio was stated to be more tha 1500:1.
43. The half-life for racemization of HMDP acid 5 was reported as 14.75 hr in refluxing aqueous alkali; Schmidt, O. T.; Demmler, K. Liebigs Ann. Chem. 1954, 585, 179.
44. The authors have deposited coordinates for structure (S)-5 with the Cambridge Data Centre. The coordinate can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
45. Model reaction of 2-phenylbenzoyl chloride (12) with sugar 3 also seemed to support this idea. Glucose 3 was reacted with 12 (1 equiv) under the same reaction conditions in entry 1 in Table 1. The esters produced were 2-benzoate (84%), 3-benzoate (5%), and 2,3-dibenzoate (3%). On the other hand, the reaction was carried out under the conditions in entry 3 in Table 1 giving 2-benzoate (36%) and 2,3-dibenzoate (28%). In both reactions, the esterification seemed to take place at the 2-position, and 3-benzoate was derived from 2-benzoate through migration by silica gel TLC monitoring experiments. The mechanistic study of this regioselective esterification of glucose 3 is now in progress. (Formula Presented) 2-Benzoate 3-Benzoate 2,3-Dibenzoate
46. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
47. Gupta, R. K.; Al-Shafi, S. M. K.; Layden, K.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1982, 2525.