A novel approach to chiral spirodiaziridines

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6391-6392

  Fioravanti, Stefania ^a   Olivieri, Lauso ^a   Pellacani, Lucio ^a   Tardella, Paolo A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Amination; Diaziridines; Strained compounds

Indexed keywords

AZIRIDINE DERIVATIVE; IMINE; SPIRODIAZIRIDINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; NUCLEAR MAGNETIC RESONANCE; PHOTOLYSIS; STEREOCHEMISTRY;

EID: 0032572907     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01317-3     Document Type: Article

References (12)

1. 1. Fioravanti, S.; Pellacani, L.; Tardella, P. A. Gazz. Chim. Ital. 1997, 127, 41-44 and our references therein.
2. 2. Fioravanti, S.; Pellacani, L.; Olivieri, L.; Tardella, P. A. J. Chem. Res., Synop. 1998, 338-339.
3. 3. D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3. 459-505; Adams, J. P. Contemporary Organic Synthesis 1997, 4, 517-543.
4. 3. D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3. 459-505; Adams, J. P. Contemporary Organic Synthesis 1997, 4, 517-543.
5. 4. Schmitz, E. in Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W.; Lwowski, W. Eds.; Pergamon Press: Oxford, 1984, Vol 7, pp 195-236.
6. 5. The same imine might behave like a base: therefore in these reaction conditions yields up to 50% can be obtained.
7. 6. Only two of the possible diastereomers were isolated, owing to stereoselective attack on one face of 1c.
8. 7. GC-MS (50-250 °C, 14 °C/min, T (Injector) = 260 °C) of each pure diastereomer always gave a mixture of both diastereomers, due to thermal equilibration. The absolute configuration has not been determined yet. Probably inversion at the alkyl substituted nitrogen must be slower than that at the ethoxycarbonyl substituted nitrogen, see also ref 4 (pp 199-201).
9. 8. Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630-3637.
10. 9. Leuenberger, C.; Hoesch, L.; Dreiding, A. S. J. Chem. Soc., Chem. Commun. 1980, 1197-1198.
11. 10. Fioravanti, S.; Pellacani, L.; Stabile, S.; Tardella, P. A.; Ballini, R. Tetrahedron 1998, 54, 6169-6179.
12. 2), 62.42 (NCH), 69.31 (NCN), 127.11, 127.80, 128.01 (Ph), 143.25 (C), 162.39 (CO).