Zinc triflate-bis-oxazoline complexes as chiral catalysts: Enantioselective reduction of α-alkoxy-ketones with catecholborane

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1601-1605

  Bandini, Marco ^a   Cozzi, Pier Giorgio ^a   de Angelis, Meri ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Asymmetric reactions; Catalysis; Ketones; Reduction

Indexed keywords

ALCOHOL DERIVATIVE; BORANE DERIVATIVE; KETONE DERIVATIVE; OXAZOLINE DERIVATIVE; REDUCING AGENT; TRIFLUOROMETHANESULFONIC ACID; ZINC COMPLEX;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; REDUCTION; TEMPERATURE;

EID: 0034603557     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02339-4     Document Type: Article

References (18)

1. Singh, V. D. Synthesis 1992, 605-617.
2. (a) Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444.
3. (b) Meier, C.; Laux, W. H. G. Tetrahedron: Asymmetry 1995, 6, 1089-1092.
4. © Cho, B. T.; Chun, Y. S. J. Org. Chem. 1998, 63, 5280-5282.
5. Takaya, H.; Ohta, T.; Noyori, R. In Asymmetric Hydrogenation. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp. 1-39.
6. Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Chem. Commun. 1999, 39-40.
7. (a) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594;
8. (b) Evans, D. A.; Kozlowski, M. C.; Murry, L. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685.
9. © Evans, D. A.; Willis, M. C.; Johnston J. N. Org. Lett. 1999, 1, 865-868.
10. Kenny, J. A.; Palmer, M. J.; Smith, A. R.; Walsgrove, T.; Wills, M. Synlett 1999, 1615-1617.
11. The box 2, 3-6 were purchased from the Aldrich Chemical Co. and the box 1, 4-5 were synthesised according to the literature: Evans, D. A.; Petersen, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. A.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
12. For the reduction of α-hydroxy-ketones, see: Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1999, 10, 1843-1846 and references cited therein.
13. Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957-8964.
14. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
15. α-Benzyloxy-ketones were prepared from the corresponding morpholine amides: Martín, R.; Romea, P.; Tey, C.; Urpí, F.; Villarasa, J. Synlett 1997, 1414-1416.
16. α-Methoxy-ketones were prepared from the reaction of the corresponding Grignard reagent with methoxyacetonitrile: Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961-1968.
17. 3), ee=99%), Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
18. Manzocchi, A.; Fiecchi, A.; Santaniello, E. Synthesis 1987, 1007-1008.