N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions

Organic Letters

Volumn 4, Issue 10, 2002, Pages 1735-1738

  Corminboeuf, Olivier ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0012126853     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257981     Document Type: Article

References (30)

1. Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1731.
2. Nishida has recently used an α,β-unsaturated Weinreb amide for an enantioselective radical cyclization with moderate success (26% ee by using 4 equiv of a chiral aluminum Lewis acid): Nishida, M.; Hayashi, H.; Nishida, A.; Kamahara, N. Chem. Commun. 1996, 579.
3. It was shown by an NMR study that Weinreb amides form mono- and bicoordinated complexes with magnesium bromide: Martin, R.; Pascual, O.; Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633.
4. 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.
5. 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; Vol. 1, pp 283-354.
6. 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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.
7. 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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.
8. 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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.
9. 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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.
10. 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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.
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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 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.; Jørgensen, K. A. J. Am. Chem Soc. 1999, 121, 3845-3853. Jensen, K. B.; Roberson, M.; Jørgensen, 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. 2 was also investigated but led to either no reaction or decomposition of the starting material.
20. For a review on the use of TADDOLs, see: Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92.
21. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
22. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
23. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
24. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
25. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
26. 4 reduction of ketones: Beck, A. K.; Dahinden, R.; Kühnle, F. N. M. ACS Symposium Series 641; American Chemical Society: Washington DC, 1996; p 52. Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croat. Chem. Acta 1996, 69, 459. Vinogradov, M. G.; Gorshkova, L. S.; Pavlov, V. A.; Mikhalev, O. V.; Chel'tsova, G. V.; Razmanov, I. V.; Ferapontov, V. A.; Malyshev, O. R.; Heise, G. L. Russ. Chem. Bull. 2000, 49, 460. Only few applications of aluminum TADDOLates as Lewis acids for enantioselective reactions have been reported: Manickam, G.; Sundararajan, G. Tetrahedron 1999, 55, 2721. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291. Fhal, A. R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
27. 4), filtered, and concentrated. The crude product was purified by flash chromatography (hexane/EtOAc 12:1).
28. For a review on chiral zinc Lewis acids, see: Motoyama, Y.; Nishiyama, H. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 59-88.
29. Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron 1986, 43, 2203.
30. 4), filtered, and concentrated. The crude product was purified by flash chromatography (hexane/EtOAc 8:1).