Iridium-catalyzed asymmetric hydrogenation of olefins with chiral N,P and C,N ligands

Topics in Organometallic Chemistry

Volumn 34, Issue , 2011, Pages 31-76

  Woodmansee, David H ^a   Pfaltz, Andreas ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

1,1 Disubstituted alkenes; Asymmetric catalysis; Asymmetric hydrogenation; Imine; Iridium N,P complexes; Tetrasubstituted alkenes; Trisubstituted alkenes

Indexed keywords

EID: 78651295903     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-15334-1_3     Document Type: Article

References (97)

1. Knowles WS (2002) Angew Chem Int Ed 41:1998
2. Blaser HU, Schmidt E (eds) (2004) Asymmetric catalysis on industrial scale. VCH, Weinheim
3. Brown JM (1999) Hydrogenation of functionalized carbon-carbon double bonds. In: Jacobsen EN, Pfaltz A, Yamamoto Y (eds) Comprehensive asymmetric catalysis, vol I. Springer, Berlin, Chapter 5.1
4. Noyori R (2002) Angew Chem Int Ed 41:2008
5. Lightfoot A, Schnider P, Pfaltz A (1998) Angew Chem Int Ed 37:2897
6. Pfaltz A, Blankenstein J, Hilgraf R, Hörmann E, McIntyre S, Menges F, Schönleber M, Smidt SP, Wüstenberg B, Zimmermann N (2002) Adv Synth Catal 345:33
7. Broene RD, Buchwald SL (1993) J Am Chem Soc 115:12569
8. Troutman MV, Appella DH, Buchwald SL (1999) J Am Chem Soc 121:4916
9. Conticello VP, Brard L, Giardello MA, Tsuji Y, Sabat M, Stern CL, Marks TJ (1992) J Am Chem Soc 114:2761
10. Crabtree RH (1979) Acc Chem Res 12:331
11. Cui X, Burgess K (2005) Chem Rev 105:3272
12. Källström K, Munslow I, Andersson PG (2006) Chem Eur J 12:3194
13. Roseblade SJ, Pfaltz A (2007) Acc Chem Res 40:1402
14. Church TL, Andersson PG (2008) Coord Chem Rev 252:513
15. Helmchen G, Pfaltz A (2000) Acc Chem Res 33:336
16. Blackmond DG, Lightfoot A, Pfaltz A, Rosner T, Schnider P, Zimmermann N (2000) Chirality 12:442
17. Smidt SP, Pfaltz A, Martínez-Viviente E, Pregosin PS, Albinati A (2003) Organometallics 22:1000
18. Krossing I, Raabe I (2004) Angew Chem Int Ed 43:2066
19. Smidt SP, Zimmermann N, Studer M, Pfaltz A (2004) Chem Eur J 10:4685
20. Wüstenberg B, Pfaltz A (2008) Adv Synth Catal 350:174
21. Crabtree RH, Demou PC, Eden D, Mihelcic JM, Parnell CA, Quirk JM, Morris GE (1982) J Am Chem Soc 104:6994
22. Mazet C, Smidt SP, Meuwly M, Pfaltz A (2004) J Am Chem Soc 126:14176
23. Burk MJ, McGrath MP, Wheeler R, Crabtree RH (1988) J Am Chem Soc 110:5034
24. Meuwly M, Roseblade SJ, Pfaltz A. University of Basel, Unpublished results
25. Roseblade SJ, Pfaltz AC (2007) R Chimie 10:178
26. Gridnev ID, Imamoto T (2004) Acc Chem Res 37:633
27. Halpern J (1982) Science 217:401
28. Brown JM, Chaloner PA (1978) J Chem Soc Chem Commun: 321
29. Feldgus S, Landis CR (2000) J Am Chem Soc 122:12714
30. Dietiker R, Chen P (2004) Angew Chem Int Ed 43:5513
31. Brandt P, Hedberg C, Andersson PG (2003) Chem Eur J 9:339
32. Hedberg C, Källström K, Brandt P, Hansen LK, Andersson PG (2006) J Am Chem Soc 128:2995
33. Fan Y, Cui X, Burgess K, Hall MB (2004) J Am Chem Soc 126:16688
34. Kaiser S, Smidt SP, Pfaltz A (2006) Angew Chem Int Ed 45:5194
35. Liu QB, Yu CB, Zhou YG (2006) Tetrahedron Lett 47:4733
36. Bell S, Wüstenberg B, Kaiser S, Menges F, Netscher T, Pfaltz A (2006) Science 311:642
37. Wang A, Wüstenberg B, Pfaltz A (2008) Angew Chem Int Ed 47:2298
38. Blankenstein J, Pfaltz A (2001) Angew Chem Int Ed 40:4445
39. Menges F, Pfaltz A (2002) Adv Synth Catal 344:40
40. Smidt SP, Menges F, Pfaltz A (2004) Org Lett 6:2023
41. Schrems MG, Pfaltz A (2009) Chem Commun 41:6210
42. Schönleber M, Hilgraf R, Pfaltz A (2008) Adv Synth Catal 350:2033
43. Li X, Li Q, Wu X, Gao Y, Xu D, Kong L (2007) Tetrahedron Asymmetry 18:629
44. Verendel JJ, Andersson PG (2007) Dalton Trans 47:5603
45. Tolstoy PI, Engman M, Paptchikhine A, Bergquist J, Church TL, Leung AWM, Andersson PG (2009) J Am Chem Soc 131:8855
46. Harmata M, Hong X (2005) Org Lett 7:3581
47. Bianco GG, Ferraz HMC, Costa AM, Costa-Lotufo LV, Pessoa CU, de Moraes MO, Schrems MG, Pfaltz A, Silva LF (2009) J Org Chem 74:2561
48. Engman M, Diesen JS, Paptchikhine A, Andersson PG (2007) J Am Chem Soc 129:4536
49. Engman M, Cheruku P, Tolstoy P, Bergquist J, Völker SF, Andersson PG (2009) Adv Synth Catal 351:375
50. Ueda M, Saitoh A, Miyaura NJ (2002) Organomet Chem 642:145
51. Morgan JB, Morken JP (2004) J Am Chem Soc 126:15338
52. Moran WJ, Morken JP (2006) Org Lett 8:2413
53. Paptchikhine A, Cheruku P, Engman M, Andersson PG (2009) Chem Commun 40:5996
54. Zhou J, Ogle JW, Fan Y, Banphavichit V, Zhu Y, Burgess K (2007) Chem Eur J 13:7162
55. Zhou J, Burgess K (2007) Angew Chem Int Ed 46:1129
56. Zhou J, Zhu Y, Burgess K (2007) Org Lett 9:1391
57. Zhu Y, Burgess K (2008) J Am Chem Soc 130:8894
58. Zhao J, Burgess K (2009) Org Lett 11:2053
59. Zhao J, Burgess K (2009) J Am Chem Soc 131:13236
60. Mantilli L, Mazet C (2009) Tetrahedron Lett 50:4141
61. Mantilli L, Gérard D, Torche S, Besnard C, Mazet C (2009) Angew Chem Int Ed 48:5143
62. Lu SM, Bolm C (2008) Chem Eur J 14:7513
63. Lu SM, Bolm C (2008) Angew Chem Int Ed 47:8920
64. Lu WJ, Chen YW, Hou XL (2008) Angew Chem Int Ed 47:10133
65. Lu WJ, Hou XL (2009) Adv Synth Catal 351:1224
66. Li S, Zhu SF, Zhang CM, Song S, Zhou QL (2008) J Am Chem Soc 130:8584
67. Cheruku P, Paptchikhine A, Church TL, Andersson PG (2009) J Am Chem Soc 131:8285
68. McIntyre S, Hörmann E, Menges F, Smidt SP, Pfaltz A (2005) Adv Synth Catal 347:282
69. Mazuela J, Verendel JJ, Coll M, Schäffner B, Börner A, Andersson PG, Pàmies O, Diéguez M (2009) J Am Chem Soc 131:12344
70. Schrems MG, Neumann E, Pfaltz A (2007) Angew Chem Int Ed 46:8274
71. Sprinz J, Helmchen G (1993) Tetrahedron Lett 34:1769
72. Zhu Y, Burgess K (2008) Adv Synth Catal 350:979
73. Cheruku P, Gohil S, Andersson PG (2007) Org Lett 9:1659
74. Zhou YG (2007) Acc Chem Res 40:1357
75. Cheruku P, Church TL, Trifonova A, Wartmann T, Andersson PG (2008) Tetrahedron Lett 49:7290
76. Baeza A, Pfaltz A (2009) Chem Eur J 15:2266
77. Hou GH, Xie JH, Yan PC, Zhou QL (2009) J Am Chem Soc 131:1366
78. Baeza A, Pfaltz A (2009) Chem Eur J 16:2036
79. Lu SM, Han XW, Zhou YG (2004) Adv Synth Catal 346:909
80. Lu SM, Bolm C (2008) Adv Synth Catal 350:1101
81. Legault CY, Charette AB (2005) J Am Chem Soc 127:8966
82. Blaser HU, Spindler F (1999) Hydrogenation of imino groups. In: Jacobsen EN, Pfaltz A, Yamamoto Y (eds) Comprehensive asymmetric catalysis, vol I. Springer, Berlin, Chapter 6.2
83. Willoughby CA, Buchwald SL (1994) J Am Chem Soc 116:11703
84. Blaser HU (2002) Adv Synth Catal 344:17
85. Schnider P, Koch G, Pretot R, Wang G, Bohnen FM, Kruger C, Pfaltz A (1997) Chem Eur J 3:887
86. Xiao D, Zhang X (2001) Angew Chem Int Ed 40:3425
87. Mršić N, Minnaard AJ, Feringa BL, Vries JG (2009) J Am Chem Soc 131:8358
88. Trifonova A, Diesen JS, Chapman CJ, Andersson PG (2004) Org Lett 6:3825
89. Trifonova A, Diesen JS, Andersson PG (2006) Chem Eur J 12:2318
90. Moessner C, Bolm C (2005) Angew Chem Int Ed 44:7564
91. Cheemala MN, Knochel P (2007) Org Lett 9:3089
92. Zhu SF, Xie JB, Zhang YZ, Li S, Zhou QL (2006) J Am Chem Soc 128:12886
93. Han Z, Wang Z, Zhang X, Ding K (2009) Angew Chem Int Ed 48:5345
94. Diéguez M, Mazuela J, Pàmies O, Verendel JJ, Andersson PG (2008) J Am Chem Soc 130:7208
95. Cheruku P, Diesen J, Andersson PG (2008) J Am Chem Soc 130:5595
96. Valla C, Baeza A, Menges F, Pfaltz A (2008) Synlett 3167
97. Baeza A, Pfaltz A (2010) Chem Eur J 16:4003