Enantioselective synthesis of allylic alcohols by the sequential aminoxylation-olefination reactions of aldehydes under ambient conditions

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1637-1639

  Zhong, Guofu ^a   Yu, Yongping ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL;

AMINOXYLATION; ARTICLE; CHEMICAL REACTION; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; OLEFINATION; SYNTHESIS;

EID: 2542595616     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049524k     Document Type: Article

References (33)

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12. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
13. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
14. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
15. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
16. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
17. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
18. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
19. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
20. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
21. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
22. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
23. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
24. For leading examples of the asymmetric synthesis of optically active allylic alcohols, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443. (b) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779. (c) Vedejs, D. E.; MacKay, J. A. Org. Lett 2001, 3, 535-536. (d) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455. (e) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468. (f) Vettel, S.; Lutz, C.; Knochel, P. Synlett 1996, 731-733. (g) Kusuda, S.; Ueno, Y.; Toru, T. Tetrahedron 1994, 50, 1045-1062. (h) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509-2512. (i) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173. (j) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710. (k) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780. (l) Fujiwara, J.; Fukatani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004-5005. (m) Noyori, R.; Tomino, I.; Tamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
25. (a) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250.
26. (b) For the subsequent similar work on the α-aminoxylation of aldehydes, see: Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. M. C. J. Am. Chem. Soc. 2003, 125, 10808-10809. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293-8296.
27. (b) For the subsequent similar work on the α-aminoxylation of aldehydes, see: Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. M. C. J. Am. Chem. Soc. 2003, 125, 10808-10809. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293-8296.
28. (c) Zhong, G. Chem. Commun. 2004, 606-607.
29. (a) Vettel, S.; Lutz, C.; Diefenbach, A.; Haderlein, G.; Hammerschmidt, S.; Kühling, K.; Mofid, M.-R.; Zimmermann, T.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 779-800.
30. (b) Heckmann, B.; Mioskowski, C.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1996, 37, 1421-1424.
31. (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039.
32. 2: C, 67.57; H, 9.92. Found: C, 67.51; H, 9.95.
33. + 256.1313, found 256.1316.