Use of diamines containing the α-phenylethyl group as chiral ligands in the asymmetric hydrosilylation of prochiral ketones

Tetrahedron

Volumn 60, Issue 8, 2004, Pages 1781-1789

  Mastranzo, Virginia M ^a,b   Quintero, Leticia ^b   De Parrodi, Cecilia Anaya ^a   Juaristi, Eusebio ^c   Walsh, Patrick J ^d  

^a UNIVERSIDAD DE LAS AMÉRICAS PUEBLA   (Mexico)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Asymmetric reactions; Chiral auxiliaries; Chiral ligands; Enantioselective hydrosilylation; Enantioselective reduction; Phenylethylamine

Indexed keywords

DIAMINE DERIVATIVE; KETONE DERIVATIVE; LIGAND; PHENYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROSILYLATION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0842310704     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.12.039     Document Type: Article

References (42)

1. Ohkuma T., Noyori R. Hydrogenation of carbonyl compounds. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive asymmetric catalysis. Vol. 1:1999;199 Springer. and Refs. 8, 9, 18, 19 and 20 therein.
2. Itsuno S., Nakano M., Miyazaki K., Masuda H., Ito K. J. Chem. Soc., Perkin Trans. 1. 1985;2039.
3. Corey E.J., Bakshi R.K., Shibata S., Chen S.P., Singh V.K. J. Am. Chem. Soc. 109:1987;7925.
4. Itsuno S. Jacobsen E.N., Pfaltz A., Yamamoto H. Hydroboration of carbonyl groups. Comprehensive asymmetric catalysis. Vol. 1:1999;267 Springer, Berlin.
5. (a) For a review, see: Nishiyama H. Jacobsen E.N., Pfaltz A., Yamamoto H. Hydrosilylation of CO and CN. Comprehensive asymmetric catalysis. Vol. 1:1999;289 Springer, Berlin.
6. Fu G., Tao B. Angew. Chem., Int. Ed. 41:2002;3892. and references cited therein.
7. Carpentier J.-F., Bette V. Curr. Org. Chem. 6:2002;913. and references cited therein.
8. For a review, see: Lawrence N.J., Drew M.D., Bushell S.M. J. Chem. Soc., Perkin Trans. 1. 1999;3381.
9. Carter M.B., Schiott B., Gutiérrez A., Buchwald S.L. J. Am. Chem. Soc. 116:1994;11667.
10. Lipshutz B.H., Noson K., Chrisman W., Lower A. J. Am. Chem. Soc. 125:2003;8799.
11. Lipshutz B.H., Caires C.C., Kuipers P., Chrisman W. Org. Lett. 5:2003;3085.
12. Mimoun H., de Saint Laumer J.Y., Giannini L., Scopelliti R., Floriani C. J. Am. Chem. Soc. 121:1999;6158.
13. Whitesell J.K. Chem. Rev. 89:1989;1581.
14. Juaristi E. Introduction to stereochemistry and conformational analysis. 1991;Wiley, New York. p 208.
15. Togni A., Venanzi L.M. Angew. Chem., Int. Ed. 33:1994;497.
16. Bennani Y.L., Hanessian S. Chem. Rev. 97:1997;3161.
17. Jaen J. Paquette L.A. Encyclopedia of reagents for organic synthesis. Vol. 5:1995;3427 Wiley, New York.
18. Juaristi E., Escalante J., León-Romo J.L., Reyes A. Tetrahedron: Asymmetry. 9:1998;715.
19. Juaristi E., León-Romo J.L., Reyes A. Tetrahedron: Asymmetry. 10:1999;2441.
20. Horner L., Dickerhof L. Liebigs Ann. Chem. 1984;124.
21. Hulst R., de Vries K., Feringa B.L. Tetrahedron: Asymmetry. 5:1995;699.
22. Anaya de Parrodi C., Moreno G.E., Quintero L., Juaristi E. Tetrahedron: Asymmetry. 9:1998;2093.
23. Potapov V.M., Koval' G.N., Solov'eva L.D. J. Org. Chem. USSR. 21:1985;705.
24. Kobayashi Y., Hayashi N., Kishi Y. Org. Lett. 4:2002;411.
25. Anaya de Parrodi C., Juaristi E., Quintero-Cortés L. An. Quim., Int. Ed. 92:1996;400.
26. Anaya de Parrodi C., Vazquez V., Quintero L., Juaristi E. Synth. Commun. 31:2001;3295.
27. Luna A., Alfonso I., Gotor V. Org. Lett. 4:2002;3627.
28. Bambridge K., Begley M.J., Simpkins N.S. Tetrahedron Lett. 35:1994;3391.
29. Dieck H., Dietrich J. Chem. Ber. 117:1984;694.
30. Alvaro G., Grepioni F., Savoia D. J. Org. Chem. 62:1997;4180.
31. Masamune S., Choy W., Petersen J.S., Sita L.R. Angew. Chem., Int. Ed. 24:1985;1.
32. Knowles W.S. Acc. Chem. Res. 16:1983;106.
33. Costa A.M., Jimeno C., Gavenonis J., Carroll P.J., Walsh P.J. J. Am. Chem. Soc. 124:2002;6929.
34. Sato S., Watanabe H., Asami M. Tetrahedron: Asymmetry. 11:2000;4329.
35. Salvi N.A., Chattopadhyay S. Tetrahedron. 57:2001;2833.
36. Huang W.-S., Hu Q.-S., Pu L. J. Org. Chem. 64:1999;7490.
37. Yong K.H., Chong M. Org. Lett. 4:2002;4139.
38. Mathre D.J., Thompson A.S., Douglas A.W., Hoogsteen K., Carroll J.D., Corley E.G., Grabowski E.J.J. J. Org. Chem. 58:1993;2880.
39. Soai K., Ookawa A., Kaba T., Ogawa K. J. Am. Chem. Soc. 109:1987;7111.
40. Naemura K., Murata M., Tanaka R., Yano M., Hirose K., Tobe Y. Tetrahedron: Asymmetry. 7:1996;3285.
41. Brown H.C., Chandrasekharan J., Ramachandran P.V. J. Am. Chem. Soc. 110:1988;1539.
42. Seebach D., Imwinkelried R., Stucky G. Helv. Chim. Acta. 70:1987;448.