The Synthesis of Chiral Phosphorus Ligands for use in Homogeneous Metal Catalysis

ChemCatChem

Volumn 3, Issue 11, 2011, Pages 1708-1730

  Lühr, Susan ^a   Holz, Jens ^a   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Asymmetric catalysis; Homogeneous catalysis; Phosphorus ligands; Synthesis

Indexed keywords

AS-LIGANDS; ASYMMETRIC CATALYSIS; CATALYZED REACTIONS; CHIRAL PHOSPHORUS LIGANDS; CHIRAL POOL; HOMOGENEOUS CATALYSIS; HYBRID LIGAND; METAL CATALYSIS; OLEFINIC GROUPS; PHOSPHORUS LIGANDS; SUPRAMOLECULAR STRUCTURE;

CATALYSIS; CHELATION; PHOSPHORUS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

LIGANDS;

EID: 84855446909     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100164     Document Type: Review

References (200)

1. Asymmetric Catalysis in Organic Synthesis (Ed.: R. Noyori), Wiley, New York, 1994;
2. Comprehensive Asymmetric Catalysis, Vol.I-III (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
3. Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley, New York, 2000.
4. Asymmetric Catalysis on Industrial Scale (Eds.: H.-U. Blaser, S. Schmidt), Wiley-VCH, Weinheim, 2004;
5. Flavours & Fragrances, March, 2011, pp.30-33.
6. L. Horner, H. Siegel, H. Buthe, Angew. Chem. 1968, 80, 1034; Angew. Chem. Int. Ed. Engl. 1968, 7, 942.
7. W. S. Knowles, M. J. Sabacky, J. Chem. Soc. Chem. Commun. 1968, 1445-1446.
8. T. P. Dang, H. B. Kagan, J. Chem. Soc. Chem. Commun. 1971, 481;
9. H. B. Kagan, T.-P. Dang, J. Am. Chem. Soc. 1972, 94, 6429-6433.
10. Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008.
11. Privileged Chiral Ligands and Catalysts (Ed.: Q.-L. Zhou), Wiley-VCH, Weinheim 2011.
12. For a recent review, see: W. Li, G. Hou, X. Sun, G. Shang, W. Zhang, X. Zhang, Pure Appl. Chem. 2010, 82, 1429-1141.
13. Parallel Synthesis of Chiral P-Ligands: L. Lefort, J. G. de Vries in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1348-1376;
14. P. E. Goudriaan, P. W. N. M. vanLeeuwen, M.-N. Birkholz, J. N. H. Reek, Eur. J. Inorg. Chem. 2008, 2939-2958;
15. J. Wassenaar, J. N. H. Reek, Org. Biomol. Chem. 2011, 9, 1704-1713.
16. L. Lefort, J. A. F. Boogers, T. Kuilman, R. J. Vijn, J. Janssen, H. Straatman, J. G. DeVries, A. H. M. DeVries, Org. Process Res. Dev. 2010, 14, 568-573.
17. L. Lefort, J. A. F. Boogers, J. G. deVries, A. H. M. DeVries, Top. Catal. 2010, 53, 1081-1086.
18. For example a screening of bridging groups effects in chelating bis(2, 5-diphenylphospholane) ligand for Rh-catalyzed asymmetric hydroformylation is described in: A. T. Axtell, J. Klosin, G. T. Whiteker, C. J. Cobley, M. E. Fox, M. Jackson, K. A. Abboud, Organometallics 2009, 28, 2993-2999.
19. A. Poater, F. Ragone, R. Mariz, R. Dorta, L. Cavallo, Chem. Eur. J. 2010, 16, 14348-14353.
20. X. Wu, P. G. Schultz, J. Am. Chem. Soc. 2009, 131, 12497-12515.
21. E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras-García, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498-6506.
22. NMR Spectroscopic Methods: W. Baumann in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1407-1432.
23. A. Fabrello, C. Dinoi, L. Perrin, P. Kalck, L. Maron, M. Urrutigoity, O. Dechy-Cabaret, Magn. Reson. Chem. 2010, 48, 848-856.
24. I. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240; Angew. Chem. Int. Ed. 2001, 40, 1197-1200;
25. Monophosphines with Chiral Backbone: C. Bruneau, J.-L. Renaud in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.5-35;
26. Monophosphinites, -aminophosphinites, -phosphonites, and -phosphoramidites: C. Bruneau, J.-L. Renaud in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.36-70.
27. L. Schiaffino, G. Ercolani, J. Phys. Org. Chem. 2011, 24, 257-261.
28. For some recent work, see: K. N. Gavrilov, S. V. Zheglov, P. A. Vologzhanin, E. A. Rastorguev, A. A. Shiryaev, M. G. Maksimova, S. E. Lyubimov, E. B. Benetsky, A. S. Safronov, P. V. Petrosvskii, V. A. Davankov, B. Schäffner, A. Börner, Russ. Chem. Bull. Int. Ed. 2008, 57, 2311-2319.
29. For recent reviews, see:
30. L. Palais, A. Alexakis, Chem. Eur. J. 2009, 15, 10473-10485;
31. J. F. Teichert, B. L. Feringa, Angew. Chem. 2010, 122, 2538-2582; Angew. Chem. Int. Ed. 2010, 49, 2486-2528.
32. K. Barta, M. Eggenstein, M. Hölscher, G. Franciò, W. Leitner, Eur. J. Org. Chem. 2009, 6198-6204.
33. K. Barta, M. Hölscher, G. Franciò, W. Leitner, Eur. J. Org. Chem. 2009, 4102-4116.
34. Atropisomeric Biaryl Diphosphine Ligands: H. Shimizu, I. Nagasaki, N. Sayo, T. Saito in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.207-259.
35. S. Doherty, C. Smyth, J. Knight (University of Newcastle upon Tyne), WO 2009/044130. See also: S. Doherty, C. H. Smyth, R. W. Harrington, W. Clegg, Organometallics 2008, 27, 4837-4840.
36. T. Korenaga, K. Osaki, R. Maenishi, T. Sakai, Org. Lett. 2009, 11, 2325-2328.
37. M.-N. Birkholz, Z. Freixa, P. W. N. M. vanLeeuwen, Chem. Soc. Rev. 2009, 38, 1099-1118;
38. P. D. Achord, P. Kiprof, B. Barker, THEOCHEM 2008, 849, 103-111.
39. J. Holz, O. Zayas, H. Jiao, W. Baumann, A. Spannenberg, A. Monsees, T. H. Riermeier, J. Almena, R. Kadyrov, A. Börner, Chem. Eur. J. 2006, 12, 5001-5013;
40. For a recent review on P-heterocycles as ligands: L. Kollár, G. Keglevich, Chem. Rev. 2010, 110, 4257-4302.
41. Z. Zhang, H. Qian, J. Longmire, X. Zhang, J. Org. Chem. 2000, 65, 6223-6226;
42. A. Lei, M. He, S. Wu, X. Zhang, Angew. Chem. 2002, 114, 3607-3610; Angew. Chem. Int. Ed. 2002, 41, 3457-3460.
43. W.-C. Yuan, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Tetrahedron 2009, 65, 4130-4141.
44. Z.-B. Luo, Q.-Z. Gong, A.-Q. Mi, X. Cui, Y.-Z. Jiang, Chem. Commun. 2002, 914-915;
45. Q.-Z. Liu, N.-S. Xie, Z.-B. Lou, X. Cui, L.-F. Cun, L. Z. Gong, A.-Q. Mi, Y.-Z. Yang, J. Org. Chem. 2003, 68, 7921-7924.
46. Practical Routes to Chiral Phospholanes: R. Kadyrov, A. Monsees in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1234-1244.
47. A. Salzer, C. Severins (RWTH Aachen), WO 2008/055963, 2008.
48. A similar cycloaddition reaction for the construction of the cyclic backbone was used by Brunner years ago in the synthesis of NORPHOS: H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 91, 655-656; Angew. Chem. Int. Ed. Engl. 1979, 18, 620-621.
49. U. Berens (Ciba Speciality Chemicals Holding Inc.), WO 2004031109, 2004.
50. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518-8519.
51. B. Zhao, X. Peng, Z. Wang, C. Xia, K. Ding, Chem. Eur. J. 2008, 14, 7847-7857.
52. A. T. Axtell, C. J. Cobley, J. Klosin, G. T. Whiteker, A. Zanotti-Gerosa, K. A. Abboud, Angew. Chem. 2005, 117, 5984-5988; Angew. Chem. Int. Ed. 2005, 44, 5834-5838.
53. T. P. Clark, C. R. Landis, S. L. Freed, J. Klosin, K. A. Abboud, J. Am. Chem. Soc. 2005, 127, 5040-5042;
54. A. L. Watkins, C. R. Landis, J. Am. Chem. Soc. 2010, 132, 10306-10317.
55. E. Vervecken, M. vanOverschelde, T. Noël, Y. Gök, S. Alvárez Rodriguez, S. Cogen, J. vanderEycken, Tetrahedron: Asymmetry 2010, 21, 2321-2328.
56. A. Rosas-Hernández, E. Vargas-Malvaez, E. Martin, L. Crespi, J. Carles Bayón, J. Mol. Catal. A 2010, 328, 68-75.
57. D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett. 2005, 7, 4907-4910;
58. Q. Dai, W. Gao, D. Liu, L. M. Kapes, X. Zhang, J. Org. Chem. 2006, 71, 3928-3934;
59. R. J. Detz, S. Arevalo Heras, R. DeGelder, P. W. N. M. vanLeeuwen, H. Hiemstra, J. N. H. Reek, J. H. vanMaarseveen, Org. Lett. 2006, 8, 3227-3230.
60. Q. Zhang, J. M. Takacs, Org. Lett. 2008, 10, 545-548.
61. K. N. Gavrilov, S. V. Zheglov, E. B. Benetsky, A. S. Safronov, E. A. Rastorguev, N. N. Groshkin, V. A. Davankov, B. Schäffner, A. Börner, Tetrahedron: Asymmetry 2009, 20, 2490-2496.
62. For a related pincer-type ligand, based on a similar motif, compare: K. N. Gavrilov, E. A. Rastorguev, A. A. Shiryaev, T. B. Grishina, A. S. Safronov, S. E. Lyubimov, V. A. Davankov, Russ. Chem. Bull. Int. Ed. 2009, 58, 1325-1327.
63. K. Gavrilov, S. V. Zheglov, E. A. Rastorguev, N. N. Groshkin, M. G. Maksimova, E. B. Benetsky, V. A. Davankov, M. T. Reetz, Adv. Synth. Catal. 2010, 352, 2599-2610.
64. Chiral Phosphine-Aminophosphines, -Phosphites, -Phosphonites, -Phosphinites, and related P/N-Ligands: N. W. Boaz, J. A. Ponasik, Jr. in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.453-476.
65. For a recent review, compare: M. Rubio, A. Pizzano, Molecules 2010, 15, 7732-7741.
66. Chiral Diphosphinites, Diphosphonites, and Mixed P, O-Ligands: C. Claver, O. Pàmies, M. Diéguez in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.506-528;
67. S. Woodward, M. Diéguez, O. Pàmies, Coord. Chem. Rev. 2010, 254, 2007-2030;
68. A. Gual, C. Godard, S. Castillón, C. Claver, Tetrahedron: Asymmetry 2010, 21, 1135-1146.
69. E. Raluy, O. Pàmies, M. Diéguez, Adv. Synth. Catal. 2009, 351, 1648-1670.
70. J. Velder, T. Robert, I. Weidner, J.-M. Neudörfl, J. Lex, H.-G. Schmalz, Adv. Synth. Catal. 2008, 350, 1309-1315.
71. J. Heinicke, R. Kadyrov, M. K. Kindermann, M. Kloss, A. Fischer, P. G. Jones, Chem. Ber. 1996, 129, 1061-1071;
72. D. Moulin, S. Bago, C. Bauduin, C. Darcel, S. Jugé, Tetrahedron: Asymmetry 2000, 11, 3939-3956.
73. T. Robert, Z. Abiri, J. Wassenaar, A. J. Sandee, S. Romanski, J.-M. Neudörfl, H.-G. Schmalz, J. N. H. Reek, Organometallics 2010, 29, 478-483.
74. J. Wassenaar, B. deBruin, J. N. H. Reek, Organometallics 2010, 29, 2767-2776.
75. F. Giancario, W. Leitner (RWTH Aachen), DE 102007059298, 2009.
76. W. Leitner, F. Francio, T. Pullmann, F. E. Hancock, A. Zanotti-Gerosa, A. Seger, B. Adger (Johnson Matthey PLC), WO 2008/041029, 2008.
77. N. Sakai, K. Nozaki, H. Takaya, Chem. Commun. 1994, 395-394;
78. H. Takaya, N. Sakai, K. Tamao, S. Mano, H. Kumobayashi, T. Tomita (Mitsubishi Gas Chemicals), EP 0614870, 1994.
79. X. Zhang, B. Cao, Y. Yan, S. Yu, B. Ji, X. Zhang, Chem. Eur. J. 2010, 16, 871-877.
80. F. Doro, J. N. H. Reek, P. W. N. M. vanLeeuwen, Organometallics 2010, 29, 4440-4447.
81. D.-Y. Wang, J.-D. Huang, X.-P. Hu, J. Deng, S.-B. Yu, Z.-C. Duan, Z. Zheng, J. Org. Chem. 2008, 73, 2011-2014.
82. Other P/N-Ligands: I. D. Kostas in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.596-632.
83. N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743-756;
84. H. Doucet, E. Fernández, T. P. Layzell, J. M. Brown, Chem. Eur. J. 1999, 5, 1320-1330;
85. J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506;
86. C. Chen, X. Li, S. L. Schreiber, J. Am. Chem. Soc. 2003, 125, 10174-10175;
87. N. Gommermann, C. Koradin, P. Knochel, Angew. Chem. 2003, 115, 5941-5944; Angew. Chem. Int. Ed. 2003, 42, 5763-5766.
88. E.g. Quinazolinap:
89. D. J. Connolly, P. M. Lacey, M. McCarthy, C. P. Saunders, A. M. Carroll, R. Goddard, P. J. Guiry, J. Org. Chem. 2004, 69, 6572-6589;
90. S. P. Flanagan, R. Goddard, P. J. Guiry, Tetrahedron 2005, 61, 9808-9821;
91. T. Fekner, H. Müller-Bunz, P. J. Guiry, Org. Lett. 2006, 8, 5109-5112;
92. A. C. Maxwell, C. Franc, L. Pouchain, H. Müller-Bunz, P. J. Guiry, Org. Biomol. Chem. 2008, 6, 3848-3853;
93. T. Fekner, H. Müller-Bunz, P. J. Guiry, Eur. J. Org. Chem. 2008, 5055-5066.
94. W. J. Fleming, H. Müller-Bunz, V. Lillo, E. Fernández, P. J. Guiry, Org. Biomol. Chem. 2009, 7, 2520-2524.
95. Chiral Bidentate Phosphorus Ligands: Hybrid Monophosphorus Ligands, P/Oxazoline Ligand: H. A. Mc Manus, D. Cusack, P. J. Guiry in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.549-596.
96. For a recent review on the synthesis and use of ferrocenyloxazolinylphosphines (FOXAPs), compare: Y. Miyake, Y. Nishibayashi, S. Uemura, Synlett 2008, 1747-1758.
97. S. K. Chakka, B. K. Peters, P. G. Andersson, G. E. M. Maguire, H. G. Kruger, T. Govender, Tetrahedron: Asymmetry 2010, 21, 2295-2301.
98. M. Schönleber, R. Hilgraf, A. Pfaltz, Adv. Synth. Catal. 2008, 350, 2033-2038.
99. C. Busacca, J. C. Lorenz (Boehringer Ingelheim Pharma GmbH & Co. KG), WO 2008/067218, 2008.
100. Reviews:
101. Chiral Spiro Diphosphines: Q.-L. Zhou, J.-H. Xie in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.329-344;
102. J.-H. Xie, Q.-L. Zhou, Acc. Chem. Res. 2008, 41, 581-593;
103. K. Ding, Z. Han, Z. Wang, Chem. Asian J. 2009, 4, 32-41.
104. J.-B. Xie, J.-H. Xie, X.-Y. Liu, W.-L. Kong, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2010, 132, 4538-4539.
105. See e.g.: S.-F. Zhu, J.-B. Xie, Y.-Z. Zhang, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 12886-12891.
106. J. B. Xie, J.-H. Xie, X.-Y. Liu, Q.-Q. Zhang, Q.-L. Zhou, Chem. Asian J. 2011, 6, 899-908.
107. M. Mauduit, D. Rix, C. Crevisy, J. Wencel (Ecole Nationale Supérieure deChimie deRennes), F 0758420, 2009;
108. J. Wencel, I. Laurent, L. Toupet, C. Crévisy, M. Mauduit, Organometallics 2010, 29, 1530-1533.
109. Compare also: K. Abdur-Rashid, D. Amoroso, R. Guo, C. Sui-Seng, C.-W. Tsang, W. Jia (Kanata Chemical Technologies Inc.), WO 2009/055912, 2009.
110. A. Börner, Eur. J. Inorg. Chem. 2001, 327-337;
111. Chiral Hydroxy Phosphines: V. Andrushko, A. Börner in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.633-714.
112. Chiral Alkoxy Phosphines: V. Andrushko, A. Börner, in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.715-748.
113. M. Watanabe, Y. Takeuchi, T. Isobe, T. Takeuchi (Daiichi Fine Chemicals Co. Ltd.), EP 1975170, 2008.
114. B. M. Trost, I. Hachiya, J. Am. Chem. Soc. 1998, 120, 1104-1105;
115. J. F. Larrow, E. N. Jacobsen, Org. Synth. 1998, 75, 1-11.
116. M. Aydemir, N. Meriç, F. Durap, A. Basal, M. Togrul, J. Organomet. Chem. 2010, 695, 1329-1398.
117. R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102;
118. M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem. 2001, 113, 2900-2903; Angew. Chem. Int. Ed. 2001, 40, 2818-2821;
119. T. Hamada, T. Torii, K. Izawa, R. Noyori, T. Ikariya, Org. Lett. 2002, 4, 4373-4376.
120. Q.-F. Wang, W. He, X.-Y. Liu, H. Chen, X.-Y. Qin, S.-Y. Zhang, Tetrahedron: Asymmetry 2008, 19, 2447-2450.
121. J. Tauchman, I. Cisarová, P. Stepnicka, Eur. J. Org. Chem. 2010, 4276-4287.
122. S. Eröksüz, Ö. Dogan, P. P. Garner, Tetrahedron: Asymmetry 2010, 21, 2535-2541.
123. B. Pugin, X. Feng, F. Spindler (Solvias AG), WO 2008/000815, 2008.
124. Ferrocene-based Diphosphines with Mixed Planar and Central Chirality: W. Chen, H.-U. Blaser in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.359-407.
125. J. Xiao, J. Ruan (Johnson Matthey Public Limited Company), WO 2009/027729, 2009.
126. Planar Chiral Ferrocene- and Paracyclophane based Diphosphines: W. Chen, H.-U. Blaser in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.345-359.
127. M. Yang, X.-B. Yang, X.-Q. Yu, ARKIVOC 2008, xvi, 84-91.
128. S. Brun, M. Parera, A. Pla-Quintana, A. Roglans, T. León, T. Achard, J. Solà, X. Verdaguer, A. Riera, Tetrahedron 2010, 66, 9032-9040.
129. For recent reviews, compare:
130. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844;
131. Phosphine-Phosphine Oxides, Phosphine-Carboxylic Acids and Phosphines Bearing Olefinic Groups: B. Schäffner, A. Börner in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.785-806;
132. P. S. Pregosin, Chem. Commun. 2008, 4875-4884; For recent synthetic work, see:
133. R. T. Stemmler, C. Bolm, Synlett 2007, 1365-1370;
134. W.-L. Duan, H. Iwamura, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 2130-2138;
135. P. Císařová, M. Lamač, P. Štěpnička, J. Organomet. Chem. 2008, 693, 446-456.
136. H. Grugel, T. Minuth, M. M. K. Boysen, Synthesis 2010, 3248-3258.
137. I. A. Shuklov, N. V. Dubrovina, H. Jiao, A. Spannenberg, A. Börner, Eur. J. Org. Chem. 2010, 1669-1680.
138. C. Müller, E. A. Pidko, A. J. P. M. Staring, M. Lutz, A. L. Spek, R. A. vanSanten, D. Vogt, Chem. Eur. J. 2008, 14, 4899-4905.
139. C. Popovici, P. Ona-Burgos, I. Fernández, L. Roces, S. Garcia-Granda, M. J. Iglesias, F. LópezOrtiz, Org. Lett. 2010, 12, 428-431.
140. J. F. Buergler, A. Togni, Chem. Commun. 2011, 47, 1896-1898.
141. E. J. Velazco, A. J. M. Caffyn, X. F. LeGoff, L. Ricard, Organometallics 2008, 27, 2402-2404.
142. Synthesis of P-Stereogenic Phosphorus Compounds based on Chiral Aminoalcohols as Chiral Auxiliary: C. Darcel, J. Uziel, S. Yugé in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1211-1233.
143. Chiral Aminophosphine-Phosphinites (AMPP): F. Agbossou-Niedercorn in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.477-505.
144. N. Khiri, E. Bertrand, M.-J. Ondel-Eymin, Y. Rousselin, J. Bayardon, P. D. Harvey, S. Jugé, Organometallics 2010, 29, 3622-3631.
145. Synthesis of P-Sterogenic Phosphines via Enantioselective Alkylation: T. Imamoto in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1201-1210.
146. T. Imamoto, Y. Kazuhiro, Y. Saito, K. Aya (Nippon Chemical Industries Co), US 2008/0221362, 2008.
147. B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachmann, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946-5952.
148. C. Jäkel, P. Hofmann, C. Scriban, P. Hanno-Igels (BASF), WO 2011/012687, 2011. See also: P. Hofmann, P. Hanno-Igels, O. Bondarev, C. Jäkel (BASF), WO 2009/101162, 2009.
149. For synergic effects of mixed N-heterocyclic carbene (NHC) and chiral P-ligands, compare: N. Toselli, D. Martin, G. Buono, Org. Lett. 2008, 10, 1453-1456.
150. A. J. Arduengo III, F. P. Gentry, Jr., P. K. Taverkere, H. E. Simmons III (E.I. du Pont deNemours and Company), US 6, 177, 575, 2001.
151. M. Revés, C. Ferrer, T. León, S. Doran, P. Etayo, A. Vidal-Ferran, A. Riera, X. Verdaguer, Angew. Chem. 2010, 122, 9642-9645; Angew. Chem. Int. Ed. 2010, 49, 9452-9455.
152. R. Aznar, G. Muller, D. Sainz, M. Font-Bardia, X. Solans, Organometallics 2008, 27, 1967-1969.
153. F. Liu, S. A. Pullarkat, K.-W. Tan, Y. Li, P.-H. Leung, Organometallics 2009, 28, 6254-6259.
154. Y. Zhang, S. A. Pullarkat, Y. Li, P.-H. Leung, Inorg. Chem. 2009, 48, 5535-5539.
155. V. V. Dunina, P. A. Zykov, M. V. Livantsov, I. V. Glukhov, K. A. Kochetkov, I. P. Glorizov, Y. K. Grishin, Organometallics 2009, 28, 425-432.
156. Chiral Secondary Phosphine Oxides and Heteroatom-Substituted Secondary Phosphine Oxides as Preligands: L. Ackermann in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.831-847.
157. T. Nemoto, Chem. Pharm. Bull. 2008, 56, 1213-1228.
158. H. Landert, F. Spindler, A. Wyss, H.-U. Blaser, B. Pugin, Y. Ribourduoille, B. Gschwend, B. Ramalingam, A. Pfaltz, Angew. Chem. 2010, 122, 7025-7028; Angew. Chem. Int. Ed. 2010, 49, 6873-6876.
159. Catalysts with Chiral Self-assembling P-Ligands: W. Seiche, B. Breit in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.848-885.
160. J. Rudolph, R. Paciello, C. Jäkel, F. Hettche, A. Börner, N. Dubrovina, M.-N. Gensow, B. Breit (BASF), WO 2008/046918, 2008;
161. I. A. Shuklov, N. V. Dubrovina, E. Barsch, R. Ludwig, D. Michalik A. Börner, Chem. Commun. 2009, 1535-1537.
162. I. A. Shuklov, N. V. Dubrovina, A. Börner, Synthesis 2007, 2925-2943.
163. J. N. H. Reek, F. W. Patureau, M. Kuil, A. J. Sandee, J. Meeuwissen (Universiteit vanAmsterdam), WO 2009/065856, 2009.
164. For reviews, compare:
165. Covalently Anchored P-Ligands and Catalysts: C. A. Sandoval, K. Ding in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.985-1029;
166. E. Framery, B. Andrioletti, M. Lemaire, Tetrahedron: Asymmetry 2010, 21, 1110-1124.
167. Dendritic Catalysts Based on Phosphorus Ligands: S. A. Heras, J. N. H. Reek in Phosphorus Ligands in Asymmetric Catalysis, Vol.I-III (Ed.: A. Börner), Wiley-VCH, Weinheim, 2008, pp.1043-1073;
168. D. Nair, H.-T. Wong, S. Han, I. F. J. Vankelecom, L. S. White, A. G. Livingston, A. T. Boam, Org. Process Res. Dev. 2009, 13, 863-869.
169. Y. Li, Y. Feng, Y.-M. He, F. Chen, J. Pan, Q.-H. Fan, Tetrahedron Lett. 2008, 49, 2878-2881.
170. M. Lamac, J. Tauchman, S. Dietrich, I. Cisarová, H. Lang, P. Stepnicka, Appl. Organomet. Chem. 2010, 24, 326-331.
171. B. H. G. Swennenhuis, R. Chen, P. W. N. M. vanLeeuwen, J. G. DeVries, P. C. J. Kamer, Eur. J. Org. Chem. 2009, 5796-5803.
172. S. Doherty, E. G. Robins, I. Pál, C. R. Newman, C. Hardacre, D. Rooney, D. A. Mooney, Tetrahedron: Asymmetry 2003, 14, 1517-1527.
173. D. Peña, A. J. Minnaard, J. G. deVries, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 14552-14553;
174. L. Lefort, J. A. F. Boogers, A. H. M. deVries, J. G. deVries, Org. Lett. 2004, 6, 1733-1735;
175. Hu, X. Ping, Z. Zheng, Org. Lett. 2005, 7, 419-422;
176. Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14212-14213;
177. L. Panella, A. M. Aleixandre, G. J. Kruidhof, J. Robertus, B. L. Feringa, J. G. deVries, A. J. Minnaard, J. Org. Chem. 2006, 71, 2026-2036.
178. S. Sahoo, P. Kumar, F. Lefebvre, S. H. Halligudi, J. Catal. 2008, 254, 91-100.
179. D. S. Glueck, Chem. Eur. J. 2008, 14, 7108-7117.