Stereo- and chemoselective transfer hydrogenation of carbonyl groups with RuCl2(PPh3)3 and BINAP-Ru as catalysts and Et3NH+H2PO2-.1,5H2O as a hydrogen donor

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6599-6602

  Bui, The Khai ^a   Arcelli, Antonio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030565528     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01476-1     Document Type: Article

References (16)

1. 1 (a) Ohkuma T.; Ooka H.; Ikariya T.; Noyori R., J. Am Chem Soc. 1995, 117, 10417.
2. (b) Bui T. K.; Arcelli A., J. Org. Chem. 1989, 54, 949;
3. (c) Bar R.; Sasson Y., Tetrahehron Lett. 1981, 22, 1710;
4. (d) Blum J.; Sasson Y.; Iflah Sh., Tetrahedron Lett. 1972, 1015;
5. (e) Watanabe Y.; Ohta T.; Tsuji Y., Bull. Chem. Soc. Jpn., 1982, 55, 2444;
6. (f) Chowdhury R. L.; Backvall J. E., J. Chem. Soc. 1991, 1063;
7. (g) Bui T. K.; Arcelli A., Tetrahedron Lett. 1985, 26, 3365;
8. (h) Brown J.M.; Brunner H.; Leitner W.; Rose M., Tetrahedron Asymmetry 1991, 2, 331;
9. (i) Bianchini C.; Farnetti E.; Graziani M.; Peruzzini M.; Polo A., Organometallics 1993, 12, 3753;
10. (j) Farnetti E.; Gulati N.V.; Graziani M., Gazz. Chim. Ital. 1993, 123, 165;
11. (k) Bui T. K. unpublished results;
12. (1) Sasson Y.; Blum J., J. Org. Chem. 1975, 40, 1887.
13. 3/C in the reaction condition without a solvent. In general, using 0.14 mol % catalyst the conversion stopped at 50%. In order to increase the conversion we used 0.5 mol % catalyst in this work (Ref 4).
14. 3 (a) Noyori R.; Ikeda T.; Ohkuma T.; Widhalm M.; Kitamura M.; Takaya H.; Akutagawa S.; Sayo N.; Saito T.; Taketomi T.; Kumobayashi H. J. Am. Chem. Soc. 1989, 111, 9134;
15. (b) Genet J.P.; Vidal V.R.; Pinel C., Synlett 1993, 478.
16. 13C-NMR spectrum based on the signal of a equatorial alcohol appearing at lower field than that for an axial alcohol).