On the lithiation of oxazolinylaziridines

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2677-2681

  Luisi, Renzo ^a,b   Capriati, Vito ^a,b   Florio, Saverio ^a,b   Ranaldo, Rosa ^a,b  

^a UNIVERSITY OF BARI   (Italy)

^b ICCOM CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; AZIRIDINYLLITHIUM; BENZENE DERIVATIVE; BENZENESULFONYL; LITHIUM; LITHIUM DERIVATIVE; OXAZOLINYLAZIRINE; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HIGH TEMPERATURE; INFRARED SPECTROSCOPY; LITHIATION; MOLECULE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOSPECIFICITY; WARMING;

EID: 0037463739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00368-X     Document Type: Article

References (23)

1. For reviews on oxiranyl and aziridinyl anion chemistry, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325; (b) Mori, Y. Reviews on Heteroatom Chemistry; Oae, S., Ed.; Tokyo, 1997; Vol. 17, pp. 183-221; (c) Mori, Y.; Yaegashy, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209; (d) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625-1642; (e) Florio, S. In Oxiranyl and Aziridinyl Anions: Applications in Synthesis. Seminars in Organic Synthesis. Società Chimica Italiana: Camerino (MC), 2001; pp. 199-225.
2. For reviews on oxiranyl and aziridinyl anion chemistry, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325; (b) Mori, Y. Reviews on Heteroatom Chemistry; Oae, S., Ed.; Tokyo, 1997; Vol. 17, pp. 183-221; (c) Mori, Y.; Yaegashy, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209; (d) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625-1642; (e) Florio, S. In Oxiranyl and Aziridinyl Anions: Applications in Synthesis. Seminars in Organic Synthesis. Società Chimica Italiana: Camerino (MC), 2001; pp. 199-225.
3. For reviews on oxiranyl and aziridinyl anion chemistry, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325; (b) Mori, Y. Reviews on Heteroatom Chemistry; Oae, S., Ed.; Tokyo, 1997; Vol. 17, pp. 183-221; (c) Mori, Y.; Yaegashy, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209; (d) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625-1642; (e) Florio, S. In Oxiranyl and Aziridinyl Anions: Applications in Synthesis. Seminars in Organic Synthesis. Società Chimica Italiana: Camerino (MC), 2001; pp. 199-225.
4. For reviews on oxiranyl and aziridinyl anion chemistry, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325; (b) Mori, Y. Reviews on Heteroatom Chemistry; Oae, S., Ed.; Tokyo, 1997; Vol. 17, pp. 183-221; (c) Mori, Y.; Yaegashy, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209; (d) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625-1642; (e) Florio, S. In Oxiranyl and Aziridinyl Anions: Applications in Synthesis. Seminars in Organic Synthesis. Società Chimica Italiana: Camerino (MC), 2001; pp. 199-225.
5. For reviews on oxiranyl and aziridinyl anion chemistry, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325; (b) Mori, Y. Reviews on Heteroatom Chemistry; Oae, S., Ed.; Tokyo, 1997; Vol. 17, pp. 183-221; (c) Mori, Y.; Yaegashy, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209; (d) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625-1642; (e) Florio, S. In Oxiranyl and Aziridinyl Anions: Applications in Synthesis. Seminars in Organic Synthesis. Società Chimica Italiana: Camerino (MC), 2001; pp. 199-225.
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12. +, 229 (18). 7: see Ref. 5.
13. CH coupling constant between the aziridine β-hydrogen (with respect to the oxazolinyl ring) and the methyl group on the α-carbon, as reported in Ref. 5.
14. 2, 100].
15. Breternitz H.J., Schaumann E., Adiwidjaja G. Tetrahedron Lett. 32:1991;1299-1302.
16. Aggarwal V.K., Alonso M., Ferrara M., Spey S.E. J. Org. Chem. 67:2002;2335-2344.
17. +, 393 (17), 229 (15).
18. Compound 7b showed a 30% of deuteration ortho to the phenyl ring of benzenesulfonyl group.
19. N-Benzenesulfonylaziridines 6 and 7 were also proved to be configurationally stable at the nitrogen atom. An attempt to provoke inversion at the nitrogen center failed. Warming in an NMR tube up to 160°C gave only decomposition. For hindered inversion of the nitrogen stereogenic center depending on the nature of the substituents and its detection, see: Gunther, H. NMR Spectroscopy: Basic Principles Concepts and Application in Chemistry, 2nd ed.; John Wiley: UK, 1995; Chapter 9, pp. 358-359.
20. -1: 2925, 1766 (C=O), 1449, 1319, 1166, 1089, 935, 752, 621, 597.
21. +, 9), 174 (20), 118 (100), 77 (21).
22. +, 64), 305 (100), 291 (25), 234 (9), 180 (61), 77 (30).
23. +, 60), 213 (33), 173 (33), 104 (100), 77 (17).