Asymmetric synthesis of axially chiral biaryls via desymmetrization of 2,2',6,6'-tetrahydroxybiphenyl using 1,4-di-O-benzyl-L-threitol as a chiral template

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1335-1343

  Tuyet, Tran Mai Thi ^a   Harada, Toshiro ^a   Hashimoto, Kazuyuki ^a   Hatsuda, Masanori ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; BIPHENYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HYDROXYBIPHENYL; LACTAM DERIVATIVE; LACTONE DERIVATIVE; PALLADIUM; REAGENT; TERPHENYL DERIVATIVE; THREITOL; TRIFLUOROMETHANESULFONIC ACID; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034629435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991364g     Document Type: Article

References (61)

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6. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
7. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
8. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
9. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
10. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
11. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
12. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
13. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
14. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
15. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
16. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
17. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
18. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
19. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
20. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
21. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
22. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
23. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
24. For the asymmetric synthesis of axially chiral biaryls, see: (a) Review: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Review: Bringmann, G.; Walter, R.; Weirich, R. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21a, p 567. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 1375. (d) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613. (e) Miyano, S.; Koike, N.; Hattori, T. Tetrahedron: Asymmetry 1994, 5, 1899. (f) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989. (g) Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993. (h) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (j) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (k) Meyers, A. I.; Meir, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. (l) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. (m) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697. (n) Kamikawa, K.; Watanabe, T.; Uemura, M. Synlett 1995, 1040. (o) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 37, 6695. (p) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375. (q) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535. (r) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700. (s) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
25. (a) Harada, T.; Ueda, S.; Yoshida, T.; Inoue, A, Takeuchi, M.; Ogawa, N.; Oku, A. J. Org. Chem. 1994, 59, 7575.
26. (b) Harada, T.; Yoshida, T.; Inoue, A.; Takeuchi, M.; Oku, A. Synlett 1995, 283.
27. (c) Harada, T.; Ueda, S.; Tuyet, T. M. T.; Inoue, A.; Fujita, K.; Takeuchi, M.; Ogawa, N.; Oku, A.; Shiro, M. Tetrahedron 1997, 53, 16663-78.
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