Boron azaenolates of chiral oxazolines: Synthesis of optically active formyl oxiranes

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7421-7425

  Florio, Saverio ^a   Capriati, Vito ^a   Luisi, Renzo ^a   Abbotto, Alessandro ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

Boron azaenolates; Chiral chlorohydrins; Chiral oxazolines; Formyl epoxides; Oxiranyl oxazolines

Indexed keywords

BORON; BORON DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; HETEROCYCLIC COMPOUND; OXAZOLINE DERIVATIVE;

ARTICLE; CHIRALITY; CROSS LINKING; DIASTEREOISOMER; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033536677     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01480-X     Document Type: Article

References (17)

1. 1. (a) Masamune, S.; Mon, S.; Van Horn, D.; Brooks, D. W. Tetrahedron Lett. 1979, 19, 1665-1668.
2. (b) Inoue, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1980, 53, 174-178.
3. 2. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
4. (b) Abdel-Magid, A.; Pridgen, L. N.; Eggleston, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595-4602.
5. (c) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39-42.
6. 3. Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162-7169.
7. 4. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613-2636.
8. 5. Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278-4279.
9. 6. Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315.
10. 7. (a) Breton, P.; Andrè-Barres, C.; Langlois, Y. Synth. Commun. 1992, 22, 2543-2554.
11. (b) Mintz, M. J.; Walling, C. Org. Synth., Collect. Vol. 5 1973, 184-187.
12. (c) Less advantageously compound 1 can be prepared from (1S,2S)-(+)-2-amino-3-methoxy-1-phenyl-1-propanol and the ethyl imidate of chloroacetonitrile. See: Meyers, A. I.; Knaus, G.; Kendall, P. M. Tetrahedron Lett. 1974, 39, 3495-3498.
13. 8. Kamata, K.; Sato, H.; Takagi, E.; Agata, I.; Meyers, A. I. Heterocycles 1999, 51, 373-378.
14. 9. Florio, S.; Capriati, V.; Luisi, R. Tetrahedron Lett. 1996, 37, 4781-4784.
15. 10. Florio, S.; Capriati, V.; Luisi, R.; Abbotto, A.; Pippel, D. J. Eur. J. Org. Chem. submitted for publication.
16. 11. When enolizable ketones are used the aldol-type reaction does not occur presumably due to the competition between the chloromethyloxazoline and the ketone towards the enolization.
17. 12. MOPAC 6.0: Stewart, J. J. P. QCPE 455, 1990. All of the calculations were performed using the AM1 Hamiltonian, with the keywords AM1, EF, and PRECISE in order to meet rigorous criteria. Geometries were optimized with no symmetry constraints.