Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes

Beilstein Journal of Organic Chemistry

Volumn 1, Issue , 2005, Pages

  Reetz, Manfred T ^a   Guo, Hongchao ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845804833     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.1186/1860-5397-1-3     Document Type: Article

References (43)

1. Gennari C, Piarulli U: Chem Rev 2003, 103:3071-3100.
2. Dahmen S, Bräse S: Synthesis 2001:1431-1449.
3. Hoveyda AH: Diversity-based identification of efficient homochiral organometallic catalysts for enantioselective synthesis. In Handbook of Combinatorial Chemistry Volume 2. Edited by: Nicolaou KC, Hanko R, Hartwig W. Weinheim: Wiley-VCH; 2002:991-1016.
4. de Vries JG, de Vries AHM: Eur J Org Chem 2003:799-811.
5. Reetz MT: Angew Chem 2001, 113:292-320.
6. Angew Chem Int Ed 2001, 40:284-310
7. Francis MB, Jacobsen EN: Angew Chem 1999, 111:987-991.
8. Angew Chem Int Ed 1999, 38:937-941
9. Berkessel A, Riedl R: J Comb Chem 2000, 2:215-219.
10. Ding K, Du H, Yuan Y, Long J: Chem Eur J 2004, 10:2872-2884.
11. Sigman MS, Jacobsen EN: J Am Chem Soc 1998, 120:4901-4902.
12. Mikami K, Yamanaka M: Chem Rev 2003, 103:3369-3400.
13. Faller JW, Lavoie AR, Parr J: Chem Rev 2003, 103:3345-3367.
14. Reetz MT, Mehler G: Angew Chem 2000, 112:4047-4049.
15. Angew Chem Int Ed 2000, 39:3889-3890
16. Reetz MT, Meiswinkel A, Mehler G, Angermund K, Graf M, Thiel W, Mynott R, Blackmond DG: J Am Chem Soc 2005, 127:10305-10313. For a study regarding the mechanism and source of enantioselectivity in Rh-catalyzed olefin-hydrogenation using BINOL-derived monodentate phosphites
17. Reetz MT, Sell T: Tetrahedron Lett 2000, 41:6333-6336.
18. Claver C, Fernandez E, Gillon A, Heslop K, Hyett DJ, Martorell A, Orpen AG, Pringle PG: Chem Commun (Cambridge UK) 2000:961-962.
19. van den Berg M, Minnaard AJ, Schudde EP, van Esch J, de Vries AHM, de Vries JG, Feringa BL: J Am Chem Soc 2000, 122:11539-11540.
20. van den Berg M, Minnaard AJ, Haak RM, Leeman M, Schudde EP, Meetsma A, Feringa BL, de Vries AHM, Maljaars CEP, Willans CE, Hyett D, Boogers JAF, Henderickx HJW, de Vries JG: Adv Synth Catal 2003, 345:308-323.
21. Bernsmann H, van den Berg M, Hoen R, Minnaard AJ, Mehler G, Reetz MT, de Vries JG, Feringa BL: J Org Chem 2005, 70:943-951.
22. Reetz MT, Sell T, Meiswinkel A, Mehler G: Angew Chem 2003, 115:814-817.
23. Angew Chem Int Ed 2003, 42:790-793
24. Reetz MT: Chim Oggi 2003, 21(10/11):5-8.
25. Reetz MT, Li X: Tetrahedron 2004, 60:9709-9714.
26. Reetz MT, Mehler G, Meiswinkel A, Sell T: Tetrahedron: Asymmetry 2004, 15:2165-2167.
27. Reetz MT, Ma J-A, Goddard R: Angew Chem 2005, 117:416-419.
28. Angew Chem Int Ed 2005, 44:412-415
29. Peña D, Minnaard AJ, Boogers JAF, de Vries AHM, de Vries JG, Feringa BL: Org Biomol Chem 2003, 1:1087-1089.
30. Reetz MT, Mehler G: Tetrahedron Lett 2003, 44:4593-4596.
31. Reetz MT, Li X: Angew Chem 2005, 117:3019-3021.
32. Angew Chem Int Ed 2005, 44:2959-2962
33. Sharpless KB: Angew Chem 2002, 114:2126-2135.
34. 3COOH and chiral ligands (tartrate being the hit). The system contains a number of Ti-species which in principle catalyze epoxidation, including achiral tert-butyl hydroperoxy-Ti-species, but it is a catalyst comprising tartrate and tert-butyl hydroperoxide which is most active and most enantioselective
35. Reetz MT, Li X: Angew Chem 2005, 117:3022-3024.
36. Angew Chem Int Ed 2005, 44:2962-2964
37. Brown JM, Naik R: J Chem Soc Chem Commun 1982:348-350.
38. Hoveyda AH, Evans DA, Fu GC: Chem Rev 1993, 93:1307-1370. Review of substrate-directable chemical reactions including hydrogenation of chiral olefins
39. Hoffmann RW: Chem Rev 1989, 89:1841-1860. Review of 1,3-allylic strain in diastereoselective reactions of chiral compounds
40. 2.
41. Ligand P15 was first prepared by G. Wilke and J. Neuffer in 1974; private communication by G. Wilke (July 19, 2005.
42. Neuffer J, Richter WJ: J Organomet Chem 1986, 301:289-297.
43. Breit B: Chem Commun (Cambridge UK) 1996:2071-2072.