Synthesis of chiral, nonracemic methyleneaziridines derived from β-amino alcohols

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3397-3406

  Ince, Julie ^a,c   Ross, Tracey M ^a   Shipman, Michael ^a,c   Ennis, David S ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PURIFICATION;

EID: 0030561557     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00447-8     Document Type: Article

References (12)

1. 2. Bottini, A.T.; Dev, V.; J. Org. Chem. 1962, 27, 968. No information concerning either the absolute configuration or the enantiomeric purity of this methyleneaziridine were disclosed.
2. 3. Quast, H.; Vélez, C.A.W.; Ang. Chem. Int. Ed. Engl. 1978, 17, 213.
3. 4. Ince, J.; Ross, T.M.; Shipman, M.; Slawin, A.M.Z.; Ennis, D.S.; Tetrahedron 1996, 52, 7037.
4. 5. Pollard, C.B.; Parcell, R.F.; J. Am. Chem. Soc. 1951, 73, 2925.
5. 6. Ager, D.J.; Prakash, I.; Schaad, D.R.; Chem. Rev. 1996, 96, 835.
6. 7. Hu, X.E.; Cassady, J.M.; Synth. Commun. 1995, 25, 907.
7. 8. Unfortunately, we have been unable to characterise any other products from this reaction.
8. 9. However, we find that the reactions are more reproducible if 15 equivalents of sodium amide are used.
9. 10. Lubell, W.D.; Rapoport, H.; J. Am. Chem. Soc. 1987, 109, 236.
10. 11. (a) Ojima, I.; Nakahashi, K.; Brandstadter, S.M.; Hatanaka, N.; J. Am. Chem. Soc. 1987,109, 1798;
11. (b) Ojima, I.; Yoda, N.; Yatabe, M.; Tanake, T.; Kogure, T.; Tetrahedron 1984, 40, 1255.
12. 12. Chang, Z.-Y.; Coates, R.M.; J. Org. Chem. 1990, 55, 3475.