Chiral P-containing palladacycle-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with alkenyl boronic acids

Synlett

Volumn , Issue 7, 2011, Pages 943-946

  Huang, Xiao Jun ^a   Mo, Dong Liang ^a   Ding, Chang Hua ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkenyl boronic acids; asymmetric catalysis; oxabicyclic alkenes; palladacycle; ring opening reaction

Indexed keywords

ALKENE DERIVATIVE; ALKENYL GROUP; BORONIC ACID DERIVATIVE; DICHLOROMETHANE; OXABICYCLIC ALKENE DERIVATIVE; PALLADACYCLE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RING OPENING;

EID: 79954575338     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259716     Document Type: Article

References (63)

1. Some reviews:, Herrmann W A., Böhm V P. W., Reisinger C P., J. Organomet. Chem. 1999 576 23
2. Bedford R B., Chem. Commun. 2003 1787
3. van der Boom M E., Milstein D, Chem. Rev. 2003 103 1759
4. Beletskaya I P., Cheprakov A V., J. Organomet. Chem. 2004 689 4055
5. Dupont J, Consorti C S., Spencer J, Chem. Rev. 2005 105 2527
6. Phan N T. S., van der Sluys M, Jones C W., Adv. Synth. Catal. 2006 348 609
7. Djukic J P., Hijazi A, Flack H D., Bernardinelli G, Chem. Soc. Rev. 2008 37 406
8. Navarro-Ranninger C, Lopez-Solera I, Perez J M., Masaguer J R., Alonso C, Appl. Organomet. Chem. 1993 7 57
9. Bincoletto C, Tersariol I L. S., Oliveira C R., Dreher S, Fausto D M., Soufen M A., Nascimento F D., Caires A C. F., Bioorg. Med. Chem. 2005 13 3047
10. Espinet P, Esteruelas M A., Oro L A., Serrano J L., Sola E, Coord. Chem. Rev. 1992 117 215
11. Beley M, Chodorowski-Kimmes S, Collin J P., Sauvage J P., Tetrahedron Lett. 1993 34 2933
12. El-Ghayourry A, Douce L, Skoulios A, Ziessel R, Angew. Chem. Int. Ed. 1998 37 1255
13. Ryabov A D., Synthesis 1985 233
14. Pfeffer M, Recl. Trav. Chim. Pays-Bas 1990 109 567
15. Pfeffer M, Pure Appl. Chem. 1992 64 335
16. Kerr P G., Leung P.-H, Wild S B., J. Am. Chem. Soc. 1987 109 4321
17. Chen Y, Smith M D., Shimizu K D., Tetrahedron Lett. 2001 42 7185
18. Hollis T K., Overman L E., Tetrahedron Lett. 1997 38 8837
19. Longmire J M., Zhang X, Shang M, Organometallics 1998 17 4374
20. Albrecht M, Kocks B M., Spek A L., van Koten G, J. Organomet. Chem. 2000 19 1282
21. Overman L E., Remarchuk T P., J. Am. Chem. Soc. 2002 124 12
22. Takenaka K, Uozumi Y, Org. Lett. 2004 6 1833
23. Kirsch S F., Overman L E., Watson M P., J. Org. Chem. 2004 69 8101
24. Kirsch S F., Overman L E., J. Am. Chem. Soc. 2005 127 2866
25. Kirsch S F., Overman L E., White N S., Org. Lett. 2007 9 911
26. Zhang T.-Z, Dai L.-X, Hou X.-L, Tetrahedron: Asymmetry 2007 18 251
27. Zhang T.-K, Mo D.-L, Dai L.-X, Hou X.-L, Org. Lett. 2008 10 3689
28. Zhang T.-K, Mo D.-L, Dai L.-X, Hou X.-L, Org. Lett. 2008 10 5337
29. Ding C.-H, Hou X.-L, Bull. Chem. Soc. Jpn. 2010 83 992
30. Yuan K, Zhang T.-K, Hou X.-L, J. Org. Chem. 2005 70 6085
31. Zhang T.-K, Yuan K, Hou X.-L, J. Organomet. Chem. 2007 692 1912
32. Navarro R, Urriolabeitia E P., Cativiela C, Diaz-de-Villegas M D., Lopez M P., Alonso E, J. Mol. Catal. A: Chem. 1996 105 111
33. Leung P H., Ng K.-H, Li Y X., White A J. P., Williams D J., Chem. Commun. 1999 2435
34. Donde Y, Overman L E., J. Am. Chem. Soc. 1999 121 2933
35. Anderson C E., Overman L E., J. Am. Chem. Soc. 2003 125 12412
36. Moyano A, Rosol M, Moreno R M., López C, Maestro M A., Angew. Chem. Int. Ed. 2005 44 1865
37. Anderson C E., Donde Y, Douglas C J., Overman L E., J. Org. Chem. 2005 70 648
38. Kirsch S F., Overman L E., J. Am. Chem. Soc. 2005 127 2866
39. Weiss M E., Fischer D F., Xin Z.-q, Jautze S, Schweizer W B., Peters R, Angew. Chem. Int. Ed. 2006 45 5694
40. Jautze S, Seiler P, Peters R, Angew. Chem. Int. Ed. 2007 46 1260
41. Fischer D F., Xin Z.-q, Peters R, Angew. Chem. Int. Ed. 2007 46 7704
42. Nomura H, Richards C J., Chem. Eur. J. 2007 13 10216
43. Suzuma Y, Yamamoto T, Ohta Y, Chem. Lett. 2007 36 470
44. Feng J.-J, Chen X.-F, Shi M, Duan W.-L, J. Am. Chem. Soc. 2010 132 5562
45. Weber M, Jautze S, Frey W, Peters R, J. Am. Chem. Soc. 2010 132 12222
46. Bravo J, Cativiela C, Navarro R, Urriolabeitia E P., J. Organomet. Chem. 2002 650 157
47. Lautens M, Synlett 1993 177
48. Lautens M, Rovis T, Tetrahedron 1999 55 8967
49. Lautens M, Fagnou K, Zunic V, Org. Lett. 2002 4 3465
50. Lautens M, Fagnou K, Hiebert S, Acc. Chem. Res. 2003 36 48
51. Madan S, Cheng C, J. Org. Chem. 2006 71 8312
52. Fan E, Shi W, Lowary T, J. Org. Chem. 2007 72 2917
53. Rehahn M, Roth M, Seggern H, Scmechel R, Ahles M, DE 102005029574 2006, Wegner S, Muellen K, Macromolecules 1993 26 3037
54. Warrener R, 1,4-Dihydro-1,4-epoxynapthalene, In Encyclopedia of Reagents for Organic Synthesis (e-EROS) Wiley-VCH Weinheim 2001
55. Bertozzi F, Pineschi M, Macchia F, Arnold L, Minnaard A, Feringa B, Org. Lett. 2002 4 2703
56. Cabrera S, Arrayas R, Alonso I, Carretero J, J. Am. Chem. Soc. 2005 127 17938
57. Cho Y, Zunic V, Senboku H, Olsen M, Lautens M, J. Am. Chem. Soc. 2006 128 6837
58. Nishimura T, Kawamoto T, Sasaki K, Tsurumaki E, Hayashi T, J. Am. Chem. Soc. 2007 129 1492
59. Webster R, Böing C, Lautens M, J. Am. Chem. Soc. 2009 131 444
60. Sakuma S, Miyaura N, J. Org. Chem. 2001 66 8944
61. Takaya Y, Ogasawara M, Hayashi T, Tetrahedron Lett. 1998 39 8497
62. Liu G.-X, Lu X.-Y, J. Am. Chem. Soc. 2006 128 16504
63. Lautens M, Dockendorff C, Fagnou K, Malicki A, Org. Lett. 2002 4 1311