Bis(phosphinite) with C2-symmetric axis; Effects on the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of acetophenone derivatives

Synlett

Volumn 23, Issue 19, 2012, Pages 2777-2784

  Aydemir, Murat ^a   Durap, Feyyaz ^a   Kayan, Cezmi ^a   Baysal, Akin ^a   Turgut, Ylmaz ^a  

^a DICLE UNIVERSITY   (Turkey)

Author keywords

enantioselectivity; homogeneous catalysis; hydrogenation; ketones; phosphinites; ruthenium

Indexed keywords

2 (BENZYLAMINO) 2 PHENYLETHAN 1 OL; 2 (BENZYLAMINO) 3 PHENYLPROPAN 1 OL; 2 [BENZYL [2 [BENZYL [1 [(DIPHENYLPHOSPHANYL)OXY] 3 PHENYLPROPAN 2 YL]AMINO]ETHYL]AMINO] 3 PHENYLPROPYL DIPHENYLPHOSPHINITE; 2 [BENZYL [2 [BENZYL [1 [(DIPHENYLPHOSPHANYL)OXY] 3 PHENYLPROPAN 2 YL]AMINO]ETHYL]AMINO] 3 PHENYLPROPYLDIPHENYLPHOSPHINITE; 2 [BENZYL [2 [BENZYL [1 [[BIS(PROPAN 2 YL)PHOSPHANYL]OXY] 3 PHENYLPROPAN 2 YL]AMINO]ETHYL]AMINO] 2 PHENYLPROPYLBIS(PROPAN 2 YL)PHOSPHINITE; 2 [BENZYL [2 [BENZYL [1 [[BIS(PROPAN 2 YL)PHOSPHANYL]OXY] 3 PHENYLPROPAN 2 YL]AMINO]ETHYL]AMINO] 3 PHENYLPROPYLBIS(PROPAN 2 YL)PHOSPHINITE; 2 [BENZYL [2 [BENZYL [1 HYDROXY 3 PHENYLPROPAN 2 YL]AMINO]ETHYL]AMINO] 3 PHENYLPROPAN 1 OL; 2 [BENZYL [2 [BENZYL [2 [(DIPHENYLPHOSPHANYL)OXY] 1 PHENYLETHYL]AMINO]ETHYL]AMINO] 2 PHENYLETHYLDIPHENYLPHOSPHINITE; 2 [BENZYL [2 [BENZYL [2 [[BIS(PROPAN 2 YL)PHOSPHANYL]OXY] 1 PHENYLETHYL]AMINO]ETHYL]AMINO] 2 PHENYLETHYLBIS(PROPAN 2 YL)PHOSPHINITE; 2 [BENZYL [2 [BENZYL [2 [[BIS(PROPAN 2 YL)PHOSPHENYL]OXY] 1 PHENYLETHYL]AMINO]ETHYL]AMINO] 2 PHENYLETHYLBIS(PROPAN 2 YL)PHOSPHINITE; 2 [BENZYL [2 [BENZYL [2 HYDROXY 1 PHENYLETHYL]AMINO]ETHYL]AMINO] 2 PHENYLETHAN 1 OL; ACETOPHENONE DERIVATIVE; AMINOALCOHOL; BIS(PHOSPHINITE); KETONE; N BENZYL AMINOALCOHOL; RUTHENIUM; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; ASYMMETRIC CATALYSIS; CAPILLARY GAS CHROMATOGRAPHY; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROGENATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 84868494591     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317505     Document Type: Article

References (48)

1. Li X., Wu X., Chen W., Hancock F. E., King F., Xiao J. Org. Lett.: 2004; 19 3321
2. Everaere K., Mortreux A., Carpentier J. F. Adv. Synth. Catal.: 2003; 345 67
3. Fan Q. H., Li Y. M., Chan A. S. C. Chem. Rev.: 2002; 102 3385
4. Blaser H. U., Malan C., Pugin B., Spindler F., Steiner H., Studer M. Adv. Synth. Catal.: 2003; 345 103
5. Noyori R., Ohkuma T. Angew. Chem. Int. Ed.: 2001; 40 40
6. Takaha H., Ohta T., Noyori R. Asymmetric Hydrogenation, In Catalytic Asymmetric Synthesis. Ojima I. VCH Berlin: 1993; 20 31
7. Noyori R. In Asymmetric Catalysis in Organic Synthesis. John Wiley New York: 1994; 1 82
8. Rajanbabu T. V., Ayers T. A., Halliday G. A., You K. K., Calabrese J. C. J. Org. Chem.: 1997; 62 6012
9. Chan A. S. C, Hu W., Pai C. C., Lau C.-P, Jiang Y., Mi A., Yan M., Sun J., Lou R., Deng J. J. J. Am. Chem. Soc.: 1997; 119 9570
10. Crabtree R. H. The Organometallic Chemistry of the Transition Metals. Wiley-Interscience New York: 2001
11. Kagan H. B., Sasaki M. Transition Metals for Organic Synthesis. Wiley-VCH Weinheim: 1998
12. Gakla P. W., Kraatz H.-B. J. Organomet. Chem.: 2003; 674 24
13. Bergmeier S. C. Tetrahedron: 2000; 56 2561
14. Ager D. J., Prakash I., Schaad D. R. Chem. Rev.: 1996; 96 835
15. Corey E. H., Helal C. J. Angew. Chem. Int. Ed.: 1998; 37 1986
16. Corey E. J., Shibata S., Bakshi R.-K. J. Am. Chem. Soc.: 1987; 109 7925
17. Kagan H.-B, Riant O. Chem. Rev.: 1992; 92 1007
18. McKennon M. J., Meyers A. I. J. Org. Chem.: 1993; 58 3568
19. Turgut Y., Hoşgören H. Tetrahedron: Asymmetry: 2003; 14 3815
20. Özbey S., Hösgören H., Turgut Y., Topal G. J. Inclusion Phenom. Macrocycl. Chem.: 2001; 39 315
21. Hauptman E., Shapiro R., Marshall W. Organometallics: 1998; 17 4976
22. Ruhlan K., Gigler P., Herdweck E. J. Organomet. Chem.: 2008; 693 874
23. Hariharasarma M., Lake C. H., Watkins C. L., Gray M. G. J. Organomet. Chem.: 1999; 580 328
24. Baysal A., Aydemir M., Durap F., Gümgüm B., Özkar S., Yildirim L. T. Polyhedron: 2007; 26 3373
25. Ceron-Camacho R., Gomez-Benitez V., Le Lagadec R., Morales-Morales D., Toscano R. A. J. Mol. Catal. A: Chem.: 2006; 247 124
26. Broger E. A., Burkart W., Hennig M., Scalone M., Schmid R. Tetrahedron: Asymmetry: 1998; 9 4043
27. Fei Z., Scopelliti R., Dyson P. J. Inorg. Chem.: 2003; 42 2125
28. Fei Z., Scopelliti R., Dyson P. J. Eur. J. Inorg. Chem.: 2004; 530
29. Bennet M. A., Robertson G. B., Smith A. K. J. Organomet. Chem.: 1972; 43 C41
30. Xie J. H., Zhou Q. L. Acc. Chem. Res.: 2008; 41 581
31. Turcry V., Pasquier C., Agbossou-Niedercorn F. C. R. Chim.: 2003; 6 179
32. Alvarez M., Lugan N., Mathieu R. J. Chem. Soc., Dalton Trans.: 1994; 2755
33. Venkatachalam G., Ramesh R. Inorg. Chem. Commun.: 2005; 8 1009
34. Francio G., Arena C. G., Panzalorto M., Bruno G., Faraone F. Inorg. Chim. Acta: 1998; 277 119
35. Chelucci G., Marchetti M., Malkov A. V., Friscourt F., Swarbrick M. E., Kocovsky P. Tetrahedron: 2011; 67 5421
36. Gao J. X., Ikariya T., Noyori R. Organometallics: 1996; 15 1087
37. Kuroki Y., Sakamaki Y., Iseki K. Org. Lett.: 2001; 3 457
38. Kuroki Y., Asada D., Sakamaki Y., Iseki K. Tetrahedron Lett.: 2000; 41 4603
39. Yang H., Alvarez M., Lugan N., Mathieu R. J. Chem. Soc., Chem. Commun.: 1995; 1721
40. Guo R., Chen X., Elphelt C., Song D., Morris R. H. Org. Lett.: 2005; 7 1757
41. Aydemir M., Meric N., Baysal A., Gümgüm B., Torul M., Turgut Y. Tetrahedron: Asymmetry: 2010; 21 703
42. Ohta T., Takaya H., Noyori R. Inorg. Chem.: 1998; 27 566
43. Grubbs R. H., DeVries R. A. Tetrahedron Lett.: 1977; 1879
44. Takehara J., Hashiguchi S., Fujii A., Inoue S., Ikariya T., Noyori R. J. Chem. Soc., Chem. Commun.: 1996; 233
45. Faller J. W., Lavoie A. R. Organometallics: 2001; 20 5245
46. Özdemir İ, Yaşar S. Transition Met. Chem.: 2005; 30 831
47. Bennet M. A., Smith A. K. J. Chem. Soc., Dalton Trans.: 1974; 233
48. Torul M., Turgut Y., Hosgören H. Chirality: 2004; 16 351