Carbon radical addition to glyoxylic oxime ether via iodine atom- transfer process

Synlett

Volumn , Issue 4, 1999, Pages 465-467

  Miyabe, Hideto ^a   Ueda, Masafumi ^a   Yoshioka, Naoko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Atom transfer; One pot; Oxime ether; Radical addition; amino acid

Indexed keywords

CARBON; ETHER DERIVATIVE; GLYCOXYLIC OXIME ETHER; IODINE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL PROCEDURES; CHEMICAL REACTION; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0032894908     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2649     Document Type: Article

References (24)

1. Recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. Snider, B. B. Chem. Rev. 1996, 96, 339.
2. Recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. Snider, B. B. Chem. Rev. 1996, 96, 339.
3. Recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. Snider, B. B. Chem. Rev. 1996, 96, 339.
4. Recent review, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. Snider, B. B. Chem. Rev. 1996, 96, 339.
5. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
6. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
7. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
8. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
9. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
10. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
11. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
12. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
13. Some examples of the synthesis of a-amino acids using glyoxylic imines through ene reactions, cycloadditions, or the nucleophilic additions of organometallic reagents or enolate anion equivalents, see: Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997. Mikami, K.; Kaneko, M.; Yajima, T. Tetrahedron Lett. 1993, 34, 4841. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431.
14. Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. I 1998, 3659. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
15. Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. I 1998, 3659. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
16. Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. I 1998, 3659. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
17. Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. I 1998, 3659. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
18. Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. I 1998, 3659. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
19. V-70(2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile)) as a radical initiator works well at room temperature. See: Kita, Y.; Sato, A.; Yamaguchi, T.; Oka, M.; Gotanda, K.; Matsugi, M. Tetrahedron Lett. 1997, 38, 3549. Kita, Y.; Gotanda, K.; Murata, K.; Suemura, M.; Sato, A. Yamaguchi, T.; Oka, M.; Matsugi, M. Org. Proc. Res. Dev. 1998, 2, 250.
20. V-70(2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile)) as a radical initiator works well at room temperature. See: Kita, Y.; Sato, A.; Yamaguchi, T.; Oka, M.; Gotanda, K.; Matsugi, M. Tetrahedron Lett. 1997, 38, 3549. Kita, Y.; Gotanda, K.; Murata, K.; Suemura, M.; Sato, A. Yamaguchi, T.; Oka, M.; Matsugi, M. Org. Proc. Res. Dev. 1998, 2, 250.
21. For a related example, see: Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780.
22. Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640. Posner, G. H. Chem. Rev. 1986, 56, 831.
23. Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640. Posner, G. H. Chem. Rev. 1986, 56, 831.
24. 4 and concentrated under reduced pressure. Purification of the residue by preparative TLC (hexane/AcOEt 15:1) afforded the α-amino acid derivatives 2.