Novel olefin-phosphorus hybrid and diene ligands derived from carbohydrates

Synthesis

Volumn , Issue 19, 2010, Pages 3248-3258

  Grugel, Holger ^a   Minuth, Tobias ^a   Boysen, Mike M K ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

asymmetric catalysis; boron; carbohydrates; ligand design; rhodium

Indexed keywords

ANOMERICS; ASYMMETRIC CATALYSIS; BORONIC ACID; CONJUGATE ADDITION; D-ARABINOSE; D-GLUCOSE; DIENE LIGANDS; HYBRID LIGAND; LIGAND DESIGN; PHOSPHINITES; PYRANOSE; UNSATURATED CARBOHYDRATES;

BORON; BORON COMPOUNDS; CARBOHYDRATES; CATALYSIS; ENANTIOSELECTIVITY; GLUCOSE; OLEFINS; PHOSPHORUS; RHODIUM;

LIGANDS;

ALKENE; ARABINOSE; BORIC ACID; CARBOHYDRATE DERIVATIVE; DIENE DERIVATIVE; GLUCOSE; LIGAND; MONOSACCHARIDE; PHOSPHINITE; PHOSPHORUS; PHOSPHORUS DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 77957131951     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258190     Document Type: Article

References (68)

1. For reviews, see:, Glorius F, Angew. Chem. Int. Ed. 2004 43 3364
2. Defieber C, Grützmacher H, Carreira E M., Angew. Chem. Int. Ed. 2008 47 4482
3. Hayashi T, Ueyama K, Tokunaga N, Yoshida K, J. Am. Chem. Soc. 2003 125 11508
4. Berthon-Gelloz G, Hayashi T, J. Org. Chem. 2006 71 8957
5. Tokunaga N, Otomaru Y, Okamato K, Ueyama K, Sintani R, Hayashi T, J. Am. Chem. Soc. 2004 126 13584
6. Otomaru Y, Okamoto K, Shintani R, Hayashi T, J. Org. Chem. 2005 70 2503
7. Defieber C, Paquin J.-F, Serna S, Carreira E M., Org. Lett. 2004 6 3873
8. Fischer C, Defieber C, Suzuki T, Carreira E M., J. Am. Chem. Soc. 2004 126 1628
9. Helbig S, Sauer S, Cramer N, Laschat S, Baro A, Frey W, Adv. Synth. Catal. 2007 349 2331
10. Wang Z.-Q, Feng C.-G, Xu M.-H, Lin G.-Q, J. Am. Chem. Soc. 2007 129 5336
11. Okamoto K, Hayashi T, Rawal V H., Org. Lett. 2008 10 4387
12. Hu X, Zhuang M, Du H, Org. Lett. 2009 11 4744
13. Deblon S, Grützmacher H, Schnberg H, WO 03/048175 A1 2003, Maire P, Maire P, Deblon S, Breher F, Geier J, Bhler C, Rüegger H, Schnberg H, Grützmacher H, Chem. Eur. J. 2004 10 4198
14. Piras E, Lng F, Rüegger H, Stein D, Wrle M, Grützmacher H, Chem. Eur. J. 2006 12 5849
15. Shintani R, Duan W.-L, Nagano T, Okada A, Hayashi T, Angew. Chem. Int. Ed. 2005 44 4611
16. Duan W.-L, Iwamura H, Shintani R, Hayashi T, J. Am. Chem. Soc. 2007 129 2130
17. Kask P, Arion V B., Widhalm M, Tetrahedron: Asymmetry 2006 17 3084
18. Defieber C, Ariger M A., Moriel P, Carreira E M., Angew. Chem. Int. Ed. 2007 46 3139
19. Stepnicka P, Cisarova I, Inorg. Chem. 2006 45 8785
20. Stepnicka P, Lamac M, Cisarova I, J. Organomet. Chem. 2008 693 446
21. Stemmler R T., Bolm C, Synlett 2007 1365
22. Takaya Y, Ogasawara M, Hayashi T, Sakai M, Miyaura N, J. Am. Chem. Soc. 1998 120 5579
23. For reviews, see:, Hayashi T, Yamasaki K, Chem. Rev. 2003 103 2829
24. Hayashi T, Pure Appl. Chem. 2004 76 465
25. Cullen W R., Sugi Y, Tetrahedron Lett. 1978 19 1635
26. Jackson R, Thompson D J., J. Organomet. Chem. 1978 159 C29
27. Selke R, React. Kinet. Catal. Lett. 1979 10 135
28. Sinou D, Descotes G, React. Kinet. Catal. Lett. 1980 14 463
29. For recent examples of carbohydrate phosphinite ligands, see:, Casalnuovo A L., RajanBabu T V., Ayers T A., Warren T H., J. Am. Chem. Soc. 1994 116 9869
30. RajanBabu T V., Ayers T A., Halliday G A., You K K., Calabrese J C., J. Org. Chem. 1997 62 6012
31. Clyne D S., Mermet-Bouvier Y C., Nomura N, RajanBabu T V., J. Org. Chem. 1999 64 7601
32. Park H, RajanBabu T V., J. Am. Chem. Soc. 2002 124 734
33. For reviews, see:, Hale K J., Rodds Chemistry of Carbon Compounds 2nd ed, 2nd Suppl., Vol. 1E/F/G Sainsbury M Elsevier Amsterdam 1993 Chap. 23b 273
34. Diéguez M, Pàmies O, Claver C, Chem. Rev. 2004 104 3189
35. Diéguez M, Claver C, Pàmies O, Eur. J. Org. Chem. 2007 4621
36. Boysen M M. K., Chem. Eur. J. 2007 13 8648
37. Benessere V, delLitto R, de Roma A, Ruffo F, Coord. Chem. Rev. 2010 254 390
38. For bis(oxazolines) derived from d -glucosamine, see:, Irmak M, Groschner A, Boysen M M. K., Chem. Commun. 2007 177
39. Irmak M, Boysen M M. K., Adv. Synth. Catal. 2008 350 403
40. Minuth T, Boysen M M. K., Synlett 2008 1483
41. Minuth T, Irmak M, Groschner A, Lehnert T, Boysen M M. K., Eur. J. Org. Chem. 2009 997
42. Minuth T, Boysen M M. K., Beilstein J. Org. Chem. 2010 6 doi:10.3762/bjoc.6.23
43. Minuth T, Boysen M M. K., Org. Lett. 2009 11 4212
44. Wolfrom M L., Thompson A, Methods Carbohydr. Chem. 1963 2 211
45. Fischer E, Ber. Dtsch. Chem. Ges. 1916 49 584
46. Mitchell S A., Pratt M R., J. Org. Chem. 2001 66 2327
47. Ferrier R J., J. Chem. Soc., Perkin Trans. 1 1979 1455
48. Ferrier R J., Overend W G., Ryan A E., J. Chem. Soc. 1962 3667
49. deFreitaFilho J R., Srivastava R M., daSilva W J. P., Cottier L, Sinou D, Carbohydr. Res. 2003 338 673
50. Hotha S, Tripathi A, J. Comb. Chem. 2005 7 968
51. Yonehara K, Hashizume T, Mori K, Ohe K, Uemura S, J. Org. Chem. 1999 64 5593
52. Yonehara K, Hashizume T, Mori K, Ohe K, Uemura S, J. Org. Chem. 1999 64 9374
53. Okamoto K, Hayashi T, Raval V H., Org. Lett. 2008 10 4387
54. DazGmez E, Brotin T, Duddeck H, Tetrahedron: Asymmetry 2007 18 2155
55. DaGmez E, Albert D, Duddeck H, Kozhushkov S I., De Meijere A, Eur. J. Org. Chem. 2006 2278
56. Krohn K, Flrke U, Gehle D, J. Carbohydr. Chem. 2002 21 431
57. Isobe M, Nishizawa R, Hosokawa S, Nishikawa T, Chem. Commun. 1998 2665
58. Alcaro S, Arena A, Neri S, Ottanà R, Ortuso F, Pavone B, Vigorita M G., Bioorg. Med. Chem. 2004 12 1781
59. Garnier E C., Liebeskind L S., J. Am. Chem. Soc. 2008 130 7449
60. Zhao J, Wei S, Ma X, Shao H, Carbohydr. Res. 2010 345 168
61. Pérez-Pérez M.-J, Doboszewiski B, Rozenski J, Herdewijn P, Tetrahedron: Asymmetry 1995 6 973
62. Marco-Contellas J, Ruiz J, Tetrahedron Lett. 1998 39 6393
63. Das S K., Reddy A K., Roy J, Synlett 2003 1607
64. Nicolaou K C., Hwang C K., Marron B E., DeFrees S A., Couladouros E A., Abe Y, Carroll P J., Snyder J P., J. Am. Chem. Soc. 1990 112 3040
65. For examples of pseudo -enantiomeric carbohydrate auxiliaries, see:, Kunz H, Pfrengle W, Sager W, Tetrahedron Lett. 1989 30 4109
66. Kunz H, Pfrengle W, Rück K, Sager W, Synthesis 1991 1039
67. For examples of pseudo -enantiomeric carbohydrate ligands, see refs 18a, 18b and, Khiar N, Fernndez I, Araffljo C S., Surez B, Alvarez E, Phosphorus, Sulfur Silicon Relat. Elem. 2005 180 1507
68. Khiar N, Araffljo C S., Surez B, Fernndez I, Eur. J. Org. Chem. 2006 1685