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Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 176-185

Asymmetric synthesis of α-amino acids based on carbon radical addition to glyoxylic oxime ether

(5) Miyabe, Hideto a Ushiro, Chikage a Ueda, Masafumi a Yamakawa, Kumiko a Naito, Takeaki a

a KOBE PHARMACEUTICAL UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; ETHER DERIVATIVE; GLYOXYLIC ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL BINDING; CHIRALITY; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0033966817 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo991353n Document Type: Article

Times cited : (158)

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- Urabe, H.¹ Yamashita, K.² Suzuki, K.³ Kobayashi, K.⁴ Sato, F.⁵

38
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- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
- (1995) Tetrahedron Lett. , vol.36 , pp. 4047-4050
- Kündig, E.P.¹ Xu, L.-H.² Romanens, P.³

39
- 0028198198
- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
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- Yamamoto, Y.¹ Onuki, S.² Yumoto, M.³ Asao, N.⁴

40
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- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
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41
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- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
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42
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- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
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- Hart, D.J.¹ Krishnamurthy, R.²

43
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- For selected examples, see: (a) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794- 7800. (c) Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 237-238. (d) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508. (e) Badone, D.; Bernassau, J.-M.; Cardamone, R.; Guzzi, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 535-537. (f) Nagano, H.; Azuma, Y. Chem. Lett. 1996, 845-846. (g) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577. (h) Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047-4050. (i) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (j) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1993, 49, 6419-6428. (k) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249-250. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470. (m) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151-1152.
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44
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45
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46
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47
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48
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