Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes

European Journal of Organic Chemistry

Volumn , Issue 11, 2001, Pages 2035-2039

  Capriati, Vito ^a   Florio, Saverio ^a   Luisi, Renzo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Asymmetric synthesis; Heterocycles; Nitrogen heterocycles; Titanium

Indexed keywords

2 CHLOROMETHYL 4 METHOXYMETHYL 5 PHENYL 2 OXAZOLINE; ALDEHYDE; ALUMINUM DERIVATIVE; BORON DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; LITHIUM DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; ISOMERISM; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034983267     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:11<2035::AID-EJOC2035>3.0.CO;2-R     Document Type: Article

References (26)

1. P. Fey, in Stereoselectire Synthesis (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Houben-Weyl, Methods in Organic Chemistry. Vol. E21b, 1995; pp 1749-1775, Thieme, Stuttgart.
2. [2a] A. Rottmann, M. Bartoczek, J. Liebscher, Synthesis 1997, 313-327.
3. [2b] A. Rottmann, J. Liebscher, Tetrahedron Lett. 1996, 37, 359-362.
4. For a review on the chemistry of oxazolines, see: A. I. Meyers, J. Heterocyclic Chem. 1998, 35, 991-1002.
5. [4a] M. Le Bail, D. J. Aitken, F. Vergne, H. P. Husson, J. Chem. Soc., Perkin Trans. 1 1997, 1681-1689.
6. [4b] P. Breton, C. André-Barrès, Y. Langlois, Synthetic Commun. 1992, 22, 2543-2554.
7. T. R. Kelly, A. Arvanitis, Tetrahedron Lett. 1984, 25, 39-42.
8. [6a] A. I. Meyers, G. Knaus, P. M. Kendall, Tetrahedron Lett. 1974, 3495-3498.
9. [6b] K. Kamata, H. Sato, E. Takagi, I. Agata, A. I. Meyers, Heterocycles 1999, 51, 373-378.
10. [6e] R. Liddell, C. G. Whiteley, J. Chem. Soc., Chem. Commun. 1983, 1535-1537.
11. [6d] R. B. English, J. R. Liddell, C. G. Whiteley, S. Afr. J. Chem. 1987, 40, 39-43.
12. [6e] J. R. Liddell, C. G. Whiteley, S. Afr. J. Chem. 1991, 44, 35-41.
13. A. Abbotto, S. Bradamante, S. Florio, V. Capriati, J. Org. Chem. 1997, 62, 8937-8940.
14. [8a] S. Florio, V. Capriati, R. Luisi, Tetrahedron Lett. 1996, 37, 4781-4784.
15. [8b] S. Florio, L. Troisi, V. Capriati, G. Coletta, Tetrahedron 1999, 35, 9859-9866.
16. [8c] S. Florio, L. Troisi, V. Capriati, G. Ingrosso, Tetrahedron Lett. 1999, 40, 6101-6104.
17. S. Florio, V. Capriati, R. Luisi, A. Abbotto, D. J. Pippel, unpublished results.
18. S. Florio, V. Capriati, R. Luisi, A. Abbotto, Tetrahedron Lett. 1999, 40, 7421-7425.
19. S. Florio, V. Capriati, R. Luisi, Tetrahedron Lett. 2000, 41, 5295-5298.
20. 2 carbon changes on going from the epoxy alcohol to the epoxy aldehyde. See: R. M. Hanson, Chem. Rev. 1991, 91, 437-475.
21. [8a] and its enantiomers showed the following retention times by chiral GC analysis: 32.80 and 33.83 min.
22. U. M. Lindstrom, P. Somfai, Synthesis 1998, 109-117.
23. [4,5,9]
24. [7,9]
25. 1H chemical shift of the vinylic proton with those of related cis- and trans-α-chlorocinnamic acids. The value found in our case (δ = 7.71) was very close to that of the Z isomer (δ = 7.87 vs. 7.18). L. A. Singer, N. P. Kong, J. Am. Chem. Soc. 1967, 89, 5251-5256.
26. J. Suffert, J. Org. Chem. 1989, 54, 509-512.