Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide

Organic Letters

Volumn 4, Issue 10, 2002, Pages 1731-1733

  Corminboeuf, Olivier ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

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ARTICLE;

EID: 0041963076     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025799t     Document Type: Article

References (57)

1. For an excellent and comprehensive treatment of the use of Lewis acids in organic synthesis, see: Lewis Acids in Organic Synthesis; Yamamoto H., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vols. 1 and 2.
2. A paper dedicated to the role of the achiral template in enantioselective reactions has been recently reported: Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
3. Quaranta, L. Ph.D. Thesis (No. 1297), Faculté des Sciences, Université de Fribourg, Switzerland, 2000. Quaranta, L.; Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 39.
4. Quaranta, L. Ph.D. Thesis (No. 1297), Faculté des Sciences, Université de Fribourg, Switzerland, 2000. Quaranta, L.; Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 39.
5. Diels-Alder reaction of acrylate-derived hydroxamic acids has been reported to take place under high pressure and has been applied as a key step in a short synthesis of peduncularine: Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333. Weinreb type acrylamides have been used in enantioselective radical cyclizations: Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. Chem. Commun. 1996, 479.
6. Diels-Alder reaction of acrylate-derived hydroxamic acids has been reported to take place under high pressure and has been applied as a key step in a short synthesis of peduncularine: Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333. Weinreb type acrylamides have been used in enantioselective radical cyclizations: Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. Chem. Commun. 1996, 479.
7. Prepared according to: Kamm, O. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I, p 445.
8. For a review, see: Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332.
9. For a review on chiral aluminum Lewis acids, see: Wulff, W. D. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 283-354.
10. Optically pure (S)- and (R)-2 are prepared according to: Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991-7994.
11. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
12. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
13. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
14. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
15. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
16. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
17. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
18. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
19. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
20. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
21. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
22. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
23. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
24. 3Al-binaphthol complexes in cycloaddition reactions has been reported. For Diels-Alder reactions, see: Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Synop. 1990, 278-279. Ketter, A.; Glahsi, G.; Herrmann, T. J. Chem. Res. Miniprint 1990, 2118-2156. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501. Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. For hetero-Diels-Alder reactions, see: Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. Hattori, K.; Yamamoto, H. Tetrahedron 1993, 49, 1749-1760. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373. Roberson, M.; Jepsen, A. S.; Jørgensen, K. A. Tetrahedron 2001, 57, 907-913. Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321. For [3 + 2] cycloaddition (aldol), see: Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911-6914. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872. For dipolar cycloaddition, see: Simonsen, K. B.; Bayon, P.; Hazel, R. G.; Gothelf, K. V.; Jorgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jorgensen, K. A. J. Org. Chem. 2000, 65, 9080-9084. For [2 + 2] cycloaddition, see: Tamai, Y.; Someya, M.; Fukumoto, J.; Niyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 1549.
25. 2 to remove the (S)-2 and hexane/EtOAc 8:1 to elute 3).
26. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
27. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
28. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
29. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
30. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
31. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
32. Ligands are available according to literature procedures. 8 and 9: Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Dotsevi, G.; Sogah, Y. J. Org. Chem. 1978, 43, 1930. 10: Gong, L.-Z.; Pu, L. Tetrahedron Lett. 2000, 41, 2327. Racemic-11: Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486. Resolution of 11: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599, 12: Dotsevi, G.; Sogah, Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035. Racemic-13: Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983. Resolution of 13: Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
33. For a review on the use of TADDOLs: Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92.
34. Corey, E. J.; Imwinkelried, T.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
35. Ishihara, K.; Kobayashi, J.; Inanaga, K.; Yamamoto, H. Synlett 2001, 3, 394.
36. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
37. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
38. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
39. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
40. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
41. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
42. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
43. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
44. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
45. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
46. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
47. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
48. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
49. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
50. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
51. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
52. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
53. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
54. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
55. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R.
56. The use of chiral heterobimetallic catalysts has been pioneered by Shibasaki; for a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. The use of polynuclear chiral Lewis acids has recently attracted much attention. Aluminum: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 110, 2347. Simpura, I.; Nevalainen, V. Angew. Chem., Int. Ed. 2000, 39, 3422. Boron: Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221. Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545. Mercury: Lee, H.; Diaz, M.; Hawthorne, M. F. Tetrahedron Lett. 1999, 40, 7651. Oh, T.; Lopez, P.; Teilly, M. Eur. J. Org. Chem. 2000, 2901. Lopez, P.; Oh, T. Tetrahdron Lett. 2000, 41, 2313. Titanium: Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusakawa, F. Organometallics 1994, 13, 2218. Hanawa, H.; Ku, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. Zirconium and hafnium: Kobayashi, S. Chirality 2000, 12, 540. Hanawa, H.; Kii. S.; Asao, N.; Maruoka, K. Tetrahedron Lett. 2000, 41, 5543. Zinc: Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibazaki, M. Org. Lett. 2001, 3, 1539. Iron: Bach, T.; Fox, N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
57. Ishihara, K.; Inanaga, K.; Kondo, S.; Funahashi, M.; Yamamoto, H. Synlett 1998, 1053.