Phosphoramidite-Controlled Asymmetric Hydrogenation with Rhodium Catalysts

By David J. Ager; André H. M. de Vries; Johannes G. de Vries

doi:10.1595/147106706X111582

ISSN: 0032-1400

oa Phosphoramidite-Controlled Asymmetric Hydrogenation with Rhodium Catalysts
Authors: By David J. Ager¹, André H. M. de Vries² and Johannes G. de Vries²
View Affiliations Hide Affiliations

Affiliations: ¹ DSM, PMB 150, 9650 Strickland Road, Suite 103, Raleigh, NC 27615U.S.A. ² DSM Research, Advanced Synthesis, Catalysis and DevelopmentPO Box 18, 6160 MD, GeleenThe Netherlands
Source: Platinum Metals Review, Volume 50, Issue 2, Apr 2006, p. 54 - 63
DOI: https://doi.org/10.1595/147106706X111582
- Published online: 01 Jan 2006

Previous Article
Table of Contents
Next Article

Abstract

Phosphoramidites, and in particular those derived from BINOL, the MonoPhos family of ligands, have proven extremely useful for the asymmetric hydrogenation of carbon–carbon unsaturation using a rhodium catalyst. Many classes of alkenes can be reduced by these catalyst systems. The use of high-throughput experimentation can be applied to the synthesis of MonoPhos ligands and their subsequent screening, in order to find an appropriate candidate for a specific transformation. Suitable mixtures of ligands can also be found by these high-throughput methods.

Article metrics loading...

/content/journals/10.1595/147106706X111582

2006-01-01

2024-12-27

Full text loading...

/deliver/fulltext/pmr/50/2/PMR-50-2-Ager.html?itemId=/content/journals/10.1595/147106706X111582&mimeType=html&fmt=ahah

References

T. P. Dang, H. B. Kagan, J. Chem. Soc. D, Chem. Comm., 1971, (10), 481 [Google Scholar]
H. B. Kagan, T. P. Dang, J. Am. Chem. Soc., 1972, 94 , (18), 6429 [Google Scholar]
W. S. Knowles, Acc. Chem. Res., 1983, 16, (3), 106 [Google Scholar]
W. S. Knowles, Angew. Chem. Int. Ed., 2002, 41, (12), 1998 [Google Scholar]
S. A. Laneman, D. J. Ager, “Handbook of Chiral Chemicals”, 2nd Edn., ed. CRC Taylor Francis, Boca Raton, 2005, p. 185 [Google Scholar]
W. Tang, X. Zhang, Chem. Rev., 2003, 103, (8), 3029 [Google Scholar]
B. L. Feringa, Acc. Chem. Res., 2000, 33, (6), 346 [Google Scholar]
J. G. de Vries, D. J. Ager, “Handbook of Chiral Chemicals”, 2nd Edn., ed. CRC Taylor Francis, Boca Raton, 2005, p. 269 [Google Scholar]
M. van den Berg, Peña D., A. J. Minnaard, B. L. Feringa, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Chim. Oggi, 2005, 22, (5), 18 [Google Scholar]
D. J. Ager, M. van den Berg, A. J. Minnaard, B. L. Feringa, A. H. M. de Vries, C. E. Willans, J. A. F. Boogers, J. G. de Vries, S. V. Malhotra, “Methods in Asymmetric Catalysis”, ed. American Chemical Society, Washington, DC, 2004, p. 115 [Google Scholar]
D. J. Ager, sp² , 2005, February, 26
D. J. Ager, J. G. de Vries, L. Lefort, A. H. M. de Vries, M. van den Berg, PharmaChem, 2004, 3, (6), 38 [Google Scholar]
T. Jerphagnon, J.-L. Renaud, C. Bruneau, Tetrahedron: Asymmetry, 2004, 15, (14), 2101 [Google Scholar]
I. V. Komarov, A. Börner, Angew. Chem. Int. Ed., 2001, 40, (7), 1197 [Google Scholar]
M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc., 2000, 122, (46), 11539 [Google Scholar]
M. van den Berg, A. J. Minnaard, R. M. Haak, M. Leeman, E. P. Schudde, A. Meetsma, B. L. Feringa, A. H. M. de Vries, C. E. P. Maljaars, C. E. Willans, D. Hyett, J. A. F. Boogers, H. J. W. Henderickx, J. G. de Vries, Adv. Synth. Catal., 2003, 345, (1–2), 308 [Google Scholar]
X. Jia, X. Li, L. Xu, Q. Shi, X. Yao, A. S. C. Chan, J. Org. Chem., 2003, 68, (11), 4539 [Google Scholar]
H. Bernsmann, M. van den Berg, R. Hoen, A. J. Minnaard, G. Mehler, M. T. Reetz, J. G. de Vries, B. L. Feringa, J. Org. Chem., 2005, 70, (3), 943 [Google Scholar]
O. Huttenloch, J. Spieler, H. Waldmann, Chem. Eur. J., 2001, 7, (3), 671 [Google Scholar]
G. Franciò, F. Faraone, W. Leitner, Angew. Chem. Int. Ed., 2000, 39, (8), 1428 [Google Scholar]
A.-G. Hu, Y. Fu, J.-H. Xie, H. Zhou, L.-X. Wang, Q.-L. Zhou, Angew. Chem. Int. Ed., 2002, 41, (13), 2348 [Google Scholar]
A. Bayer, P. Murszat, U. Thewalt, B. Rieger, Eur. J. Inorg. Chem., 2002, (10), 2614 [Google Scholar]
Q. Zeng, H. Liu, X. Cui, A. Mi, Y. Jiang, X. Li, M. C. K. Choi, A. S. C. Chan, Tetrahedron: Asymmetry, 2002, 13, (2), 115 [Google Scholar]
Y. Liu, K. Ding, J. Am. Chem. Soc., 2005, 127, (30), 10488 [Google Scholar]
S. Wu, W. Zhang, Z. Zhang, X. Zhang, Org. Lett., 2004, 6, (20), 3565 [Google Scholar]
M. T. Reetz, J.-A. Ma, R. Goddard, Angew. Chem. Int. Ed., 2005, 44, (3), 412 [Google Scholar]
X.-P. Hu, Z. Zheng, Org. Lett., 2004, 6, (20), 3585 [Google Scholar]
X. Jia, X. Li, W. S. Lam, S. H. L. Kok, L. Xu, G. Lu, C.-H. Yeung, A. S. C. Chan, Tetrahedron: Asymmetry, 2004, 15, (14), 2273 [Google Scholar]
N. W. Boaz, J. A. Ponasik, S. E. Large, Tetrahedron: Asymmetry, 2005, 16, (12), 2063 [Google Scholar]
Q.-H. Zeng, X.-P. Hu, Z.-C. Duan, X.-M. Liang, Z. Zheng, Tetrahedron: Asymmetry, 2005, 16, (6), 1233 [Google Scholar]
R. Hoen, M. van den Berg, H. Bernsmann, A. J. Minnaard, J. G. de Vries, B. L. Feringa, Org. Lett., 2004, 6, (9), 1433 [Google Scholar]
S. Doherty, E. G. Robins, I. Pál, C. R. Newman, C. Hardacre, D. Rooney, D. A. Mooney, Tetrahedron: Asymmetry, 2003, 14, (11), 1517 [Google Scholar]
C. Simons, U. Hanefeld, I. W. C. E. Arends, A. J. Minnaard, T. Maschmeyer, R. A. Sheldon, Chem. Commun., 2004, (24), 2830 [Google Scholar]
P. N. M. Botman, A. Amore, R. van Heerbeek, J. W. Back, H. Hiemstra, J. N. H. Reek, J. H. van Maarseveen, Tetrahedron Lett., 2004, 45, (31), 5999 [Google Scholar]
X. Jia, R. Guo, X. Li, X. Yao, A. S. C. Chan, Tetrahedron Lett., 2002, 43, (32), 5541 [Google Scholar]
M. van den Berg, R. M. Haak, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Adv. Synth. Catal., 2002, 344, (9), 1003 [Google Scholar]
S.-F. Zhu, Y. Fu, J.-H. Xie, B. Liu, L. Xing, Q.-L. Zhou, Tetrahedron: Asymmetry, 2003, 14, (20), 3219 [Google Scholar]
X. Li, X. Jia, G. Lu, T. T.-L. Au-Yeung, K.-H. Lam, T. W. H. Lo, A. S. C. Chan, Tetrahedron: Asymmetry, 2003, 14, (18), 2687 [Google Scholar]
J. You, H.-J. Drexler, S. Zhang, C. Fischer, D. Heller, Angew. Chem. Int. Ed., 2003, 42, (8), 913 [Google Scholar]
D. Peña, A. J. Minnaard, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc., 2002, 124, (49), 14552 [Google Scholar]
L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Org. Lett., 2004, 6, (11), 1733 [Google Scholar]
X.-P. Hu, Z. Zheng, Org. Lett., 2005, 7, (3), 419 [Google Scholar]
L. Panella, B. L. Feringa, J. G. de Vries, A. J. Minnaard, Org. Lett., 2005, 7, (19), 4177 [Google Scholar]
R. Hoen, J. A. F. Boogers, H. Bernsmann, A. J. Minnaard, A. Meetsma, T. D. Tiemersma, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Angew. Chem. Int. Edn., 2005, 44, (27), 4209 [Google Scholar]
R. Hulst, N. K. de Vries, B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, (4), 699 [Google Scholar]
A. H. M. de Vries, A. Meetsma, B. L. Feringa, Angew. Chem. Int., Edn. Eng., 1996, 35, (20), 2374 [Google Scholar]
L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron, 2000, 56 , (18), 2865 [Google Scholar]
J. G. de Vries, A. H. M. de Vries, Eur. J. Org. Chem., 2003, (5), 799 [Google Scholar]
Y. H. Choi, J. Y. Choi, H. Y. Yang, Y. H. Kim, Tetrahedron: Asymmetry, 2002, 13, (8), 801 [Google Scholar]
Y. Fu, X.-X. Guo, S.-F. Zhu, A.-G. Hu, J.-H. Xie, Q.-L. Zhou, J. Org. Chem., 2004, 69, (14), 4648 [Google Scholar]
M. van den Berg, University of Groningen, 2006
D. Peña, A. J. Minnaard, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Biomol. Chem., 2003, 1, (7), 1087 [Google Scholar]
M. T. Reetz, T. Sell, Meiswinkel A., G. Mehler, Angew. Chem. Int. Edn., 2003, 42, (7), 790 [Google Scholar]
C. Monti, Gennari C., U. Piarulli, Tetrahedron Lett., 2004, 45, (37), 6859 [Google Scholar]
C. Monti, C. Gennari, U. Piarulli, J. G. de Vries, A. H. M. de Vries, L. Lefort, Chem. Eur. J., 2005, 11, (22), 6701 [Google Scholar]
D. Peña, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Lett., 2003, 5, (4), 475 [Google Scholar]
C. J. Cobley, I. C. Lennon, C. Praquin, Zanotti-Gerosa A., R. B. Appell, C. T. Goralski, A. C. Sutterer, Org. Process Res. Dev., 2003, 7, (3), 407 [Google Scholar]
A. Duursma, J.-G. Boiteau, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa, J. Org. Chem., 2004, 69, (23), 8045 [Google Scholar]
A. Duursma, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa, Org. Biomol. Chem., 2004, 2, (12), 1682 [Google Scholar]

/content/journals/10.1595/147106706X111582

Phosphoramidite-Controlled Asymmetric Hydrogenation with Rhodium Catalysts

Platinum Metals Review 50, 54 (2006); https://doi.org/10.1595/147106706X111582

/content/journals/10.1595/147106706X111582

Data & Media loading...

Article Type: Research Article

Most Cited Most Cited RSS feed

- Metal-Ligand Exchange Kinetics in Platinum and Ruthenium Complexes
  
  By By Jan Reedijk
- The Preparation of Palladium Nanoparticles
  
  By By James Cookson
- Diesel Engine Emissions and Their Control
  
  By By Tim Johnson
- Recycling the Platinum Group Metals: A European Perspective
  
  By By Christian Hagelüken
- Palladium-Based Alloy Membranes for Separation of High Purity Hydrogen from Hydrogen-Containing Gas Mixtures
  
  Authors: By Gennady S. Burkhanov, Nelli B. Gorina, Natalia B. Kolchugina, Nataliya R. Roshan, Dmitry I. Slovetsky and Evgeny M. Chistov
- A Healthy Future: Platinum in Medical Applications
  
  Authors: By Alison Cowley and and Brian Woodward*
- A Review of the Behaviour of Platinum Group Elements within Natural Magmatic Sulfide Ore Systems
  
  Authors: By D. A. Holwell and I. McDonald
- FINAL ANALYSIS
  
  By
- Asymmetric Transfer Hydrogenation in Water with Platinum Group Metal Catalysts
  
  Authors: By Xiaofeng Wu, Chao Wang and Jianliang Xiao
- Carbon Nanotubes as Supports for Palladium and Bimetallic Catalysts for Use in Hydrogenation Reactions
  
  Authors: R. S. Oosthuizen and V. O. Nyamori
More Less

oa Phosphoramidite-Controlled Asymmetric Hydrogenation with Rhodium Catalysts

Abstract

Most Read This Month

Most Cited Most Cited RSS feed