Diastereoselective cycloadditions involving methyleneaziridines: Reactions with tetracyanoethylene

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 6091-6092

  Shipman, Michael ^a   Ross, Tracey M ^b   Slawin, Alexandra M Z ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; HEXANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE SENSITIVITY; X RAY CRYSTALLOGRAPHY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033551719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01267-8     Document Type: Article

References (9)

1. Present address: School of Chemistry, University of St Andrews, St Andrews, Fife, Scotland, KY16 9ST.
2. For a leading reference on the preparation and chemistry of methyleneaziridines, see De Kimpe N, De Smaele D, Sakonyi Z. 1997. J. Org. Chem. 62, 2448.
3. 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.
4. Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925.
5. Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462.
6. Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397.
7. Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T. J. Chem. Soc. (C) 1967, 928.
8. For clarity, all methyleneaziridines (and cycloadducts) are shown possessing the (R)-configuration of the N- substituent. In fact, these studies were performed using (R)-2a; (±)-2b; (S)-2c; (R)-2d; (±)-2e. All the cycloadducts are shown with correct relative configurations.
9. All new compounds gave satisfactory spectroscopic and high resolution mass spectral data.