A New N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromide Consisting of 4,6-Disubstituted Biphenyl Subunit as an Efficient Chiral Phase-Transfer Catalyst

Synlett

Volumn , Issue 12, 2003, Pages 1931-1933

  Ooi, Takashi ^a   Kubota, Yasushi ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkylation; Biphenyl subunit; Chiral quaternary ammonium bromide; Glycine ester Schiff base; amino acids

Indexed keywords

BROMIDE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; PHASE TRANSITION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0142059745     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41478     Document Type: Article

References (31)

1. (a) Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446.
2. (b) See also: Bhattacharya, A.; Dolling, U.-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 476.
3. (c) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
4. For reviews: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic and Professional: London, 1997, Chap. 14. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 123. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3. (e) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
5. For reviews: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic and Professional: London, 1997, Chap. 14. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 123. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3. (e) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
6. For reviews: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic and Professional: London, 1997, Chap. 14. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 123. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3. (e) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
7. For reviews: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic and Professional: London, 1997, Chap. 14. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 123. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3. (e) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
8. For reviews: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic and Professional: London, 1997, Chap. 14. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000, 123. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3. (e) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
9. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
10. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
11. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
12. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
13. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
14. For representative examples, see: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. (c) Jew, S.-S.; Jeong, B.-S.; Yoo, M-S.; Huh, H.; Park, H.- G. Chem. Commun. 2001, 1244. (d) Chinchilla, R.; Mazón, P.; Nájera, C. Tetrahedron: Asymmetry 2002, 13, 927. (e) Park, H.-G.; Jeong, B.-S.; Yoo, M-S.; Lee, J.-H.; Park, M-K.; Lee, Y.-J.; Kim, M-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036. (f) Jew, S.-S.; Yoo, M-S.; Jeong, B.-S.; Park, Y. II; Park, H.-G. Org. Lett. 2002, 4, 4245.
15. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
16. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
17. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
18. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
19. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
20. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
21. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
22. 1,1′-Binaphthyl derivatives: (a) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Vyskocil, S.; Kagan, H. B. Tetrahedron: Asymmetry 1999, 10, 1723. (c) Tartaric acid derivatives: Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (d) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (e) Guanidine derivatives: Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem. Int. Ed. 2002, 41, 2832. (f) Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2001, 57, 8959. (g) Metal-salen complexes: Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105. (h) Belokon, Y. N.; Davies, R. G.; North, M. Tetrahedron Lett. 2000, 41, 7245.
23. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
24. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
25. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
26. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
27. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
28. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
29. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
30. For our recent contributions, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640. (g) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem. Int. Ed. 2002, 41, 4542. (h) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579.
31. +).