Generation of threonine- and azathreonine N-carboxy anhydrides from α-hydroxy β-lactams promoted by 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) in combination with sodium hypochlorite

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4400-4404

  Palomo, Claudio ^a   Aizpurua, Jesús M ^a   Cuevas, Carmen ^a   Urchegui, Raquel ^a   Linden, Anthony ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030018754     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952178n     Document Type: Article

References (38)

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9. For reviews, see: (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1993. (b) α-Amino Acid Synthesis; O'Donell, H. J., Ed.; Tetrahedron Symposia-in-print, Tetrahedron 1988, 44, 5253. (c) Shioiri, T.; Hamada, Y. Heterocycles 1988, 27, 1035. (d) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238. (e) Cintas, P. Tetrahedron 1991, 47, 6079. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (g) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 2, 173. (h) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
10. For reviews, see: (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1993. (b) α-Amino Acid Synthesis; O'Donell, H. J., Ed.; Tetrahedron Symposia-in-print, Tetrahedron 1988, 44, 5253. (c) Shioiri, T.; Hamada, Y. Heterocycles 1988, 27, 1035. (d) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238. (e) Cintas, P. Tetrahedron 1991, 47, 6079. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (g) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 2, 173. (h) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
11. For reviews, see: (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1993. (b) α-Amino Acid Synthesis; O'Donell, H. J., Ed.; Tetrahedron Symposia-in-print, Tetrahedron 1988, 44, 5253. (c) Shioiri, T.; Hamada, Y. Heterocycles 1988, 27, 1035. (d) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238. (e) Cintas, P. Tetrahedron 1991, 47, 6079. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (g) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 2, 173. (h) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
12. For reviews, see: (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1993. (b) α-Amino Acid Synthesis; O'Donell, H. J., Ed.; Tetrahedron Symposia-in-print, Tetrahedron 1988, 44, 5253. (c) Shioiri, T.; Hamada, Y. Heterocycles 1988, 27, 1035. (d) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238. (e) Cintas, P. Tetrahedron 1991, 47, 6079. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (g) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 2, 173. (h) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
13. For reviews, see: (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1993. (b) α-Amino Acid Synthesis; O'Donell, H. J., Ed.; Tetrahedron Symposia-in-print, Tetrahedron 1988, 44, 5253. (c) Shioiri, T.; Hamada, Y. Heterocycles 1988, 27, 1035. (d) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238. (e) Cintas, P. Tetrahedron 1991, 47, 6079. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (g) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 2, 173. (h) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
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25. 19F NMR spectra.
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33. -1. The structure was solved by direct methods and refined on F by full-matrix least-squares methods to give R = 0.0513, wR = 0.0460, S = 1.686 using 1635 observed reflections with I > 2σ(I) from the 2460 collected with 5° < 2θ < 55°. The enantiomorph was fixed by the known S configuration at C5 in the pyrrolidine ring. The atomic coordinates have been deposited at the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
34. For the use of β-lactams in amino acid and natural product synthesis, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. In The Organic Chemistry of β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1992; p 197. (c) Ojima, I. Acc. Chem. Res. 1995, 383. (d) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991. (e) Reference 2h.
35. For the use of β-lactams in amino acid and natural product synthesis, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. In The Organic Chemistry of β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1992; p 197. (c) Ojima, I. Acc. Chem. Res. 1995, 383. (d) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991. (e) Reference 2h.
36. For the use of β-lactams in amino acid and natural product synthesis, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. In The Organic Chemistry of β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1992; p 197. (c) Ojima, I. Acc. Chem. Res. 1995, 383. (d) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991. (e) Reference 2h.
37. For the use of β-lactams in amino acid and natural product synthesis, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. In The Organic Chemistry of β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1992; p 197. (c) Ojima, I. Acc. Chem. Res. 1995, 383. (d) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991. (e) Reference 2h.
38. For the use of β-lactams in amino acid and natural product synthesis, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. In The Organic Chemistry of β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1992; p 197. (c) Ojima, I. Acc. Chem. Res. 1995, 383. (d) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991. (e) Reference 2h.