Novel ring opening reactions of methyleneaziridines

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5887-5890

  Ince, Julie ^a   Shipman, Michael ^a   Ennis, David S ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AZIRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030820798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01311-7     Document Type: Article

References (13)

1. For a leading reference on the preparation and chemistry of methyleneaziridines, see De Kimpe, N.; De Smaele, D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448-2452.
2. Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925-2927.
3. Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc 1957, 79, 1462-1464.
4. Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037-7044.
5. Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397-3406.
6. Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66-69.
7. Quast, H.; Weise Vélez, C. A. Angew. Chem. Int. Ed. Engl. 1974, 13, 342-343.
8. Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045-2047.
9. All new compounds gave satisfactory spectroscopic and high resolution mass spectral data.
10. 2 requires 253.0870.
11. Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron 1994, 50, 3889-3904.
12. Attempts to react sterically encumbered N-trityl methyleneaziridine under these reaction conditions were unsuccessful. The starting methyleneaziridine was recovered unchanged.
13. Quast, H.; Weise Vélez, C. A. Angew. Chem. Int. Ed. Engl. 1978, 17, 213-214.