One-pot synthesis of α-amino acids based on free radical-mediated carbon-carbon bond formation

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 22, 1998, Pages 3659-3660

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

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748731177     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807017b     Document Type: Article

References (18)

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6. (b) N. A. Petasis, A. Goodman and I. A. Zavialov, Tetrahedron, 1997, 53, 16463.
7. (a) H. Miyabe, R. Shibata, C. Ushiro and T. Naito, Tetrahedron Lett., 1998, 39, 631;
8. (b) H. Miyabe, C. Ushiro and T. Naito, Chem. Commun., 1997, 1789;
9. (c) H. Miyabe, R. Shibata, M. Sangawa, C. Ushiro and T. Naito, Tetrahedron, 1998, 54, 11431.
10. Oxime ethers are well known to be excellent radical acceptors because of the extra stabilisation of the intermediate aminyl radical provided by the adjacent oxygen atom. See H. Miyabe, M. Torieda, K. Inoue, K. Tajiri, T. Kiguchi and T. Naito, J. Org. Chem., 1998, 63, 4397 and references cited therein.
11. For a related example, high 1,3-stereoinductiori in radical additions to glyoxylate imines has recently been reported. See M. P. Bertrand, L. Feray, R. Nouguier and L. Stella, Synlett, 1998, 780.
12. K. Nozaki, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1991, 64, 403.
13. (a) Y. Yamamoto and W. Ito, Tetrahedron, 1988, 44, 5415;
14. (b) T. Kolasa, S. K. Sharma and M. J. Miller, Tetrahedron, 1988, 44, 5431;
15. (c) J.-C. Fiaud and H. B. Kagan, Tetrahedron Lett., 1971, 1019;
16. (d) J.-C. Fiaud and H. B. Kagan, Tetrahedron Lett., 1970, 1813.
17. For recent examples, the nucleophilic addition of allylic zinc reagents to glyoxylic oxime ethers proceeds regioselectively to give the C-alkylated products. See (a) S. Hanessian and R.-Y. Yang, Tetrahedron Lett., 1996, 37, 8997;
18. (b) S. Hanessian and R.-Y. Yang, Tetrahedron Lett., 1996, 37, 5273.