Instant ligand libraries. Parallel synthesis of monodentate phosphoramidites and in situ screening in asymmetric hydrogenation

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1733-1735

  Lefort, Laurent ^a   Boogers, Jeroen A F ^a   De Vries, André H M ^a   De Vries, Johannes G ^a  

^a DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANILINE DERIVATIVE; LIGAND; METAL;

ARTICLE; AUTOMATION; CATALYSIS; CHIRALITY; HYDROGENATION; PRECURSOR; SCREENING; STEREOCHEMISTRY; SYNTHESIS;

AMIDES; AMINES; AMINO ACIDS; CATALYSIS; HYDROGENATION; LIGANDS; MOLECULAR STRUCTURE; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 2942599460     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049510e     Document Type: Article

References (24)

1. (a) Gennari, C.; Piarulli, U. Chem. Rev. 2003, 103, 3071.
2. (b) de Vries, J. G.; de Vries, A. H. M. Eur. J. Org. Chem. 2003, 799.
3. (c) Archibald, B.; Brümmer, O.; Devenney, M.; Gorer, S.; Jandeleit, B.; Uno, T.; Weinberg, W. H.; Weskamp. T. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 2, p 885.
4. (d) Hoveyda, A. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 2, p 991.
5. Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
6. (a) de Vries, A. H. M.; Pineschi, M.; Arnold, L. A.; Imbos, R.; Feringa, B. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620.
7. (b) Feringa, B. L. Acc. Chem. Res. 2002, 33, 346.
8. (c) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
9. (d) van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Willans, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308.
10. (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
11. (f) Boiteau, J. G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681.
12. (g) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
13. (h) Jensen, J. F.; Svendsen, Y.; la Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558.
14. (i) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
15. (j) Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
16. (k) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272.
17. (l) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
18. (m) Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 930.
19. Jia, X.; Li, X.; Xu, L.; Shi, Q.; Yao, X.; Chan, A. S. C. J. Org. Chem. 2003, 65, 4539.
20. See the Supporting Information.
21. This reactor was developed by Premex in cooperation with DSM. See: www.premex-reactorag.ch/e/spezialloesungen/produkteneuheiten/.
22. Heller, D.; Drexler H.-J.; Spannenberg, A.; Heller, B.; You, J.; Baumann, W. Angew. Chem., Int. Ed. 2002, 41, 777 and references therein.
23. We expect that this method can be easily extended to the monodentate phosphonites (Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961) and phosphites (Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889).
24. We expect that this method can be easily extended to the monodentate phosphonites (Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961) and phosphites (Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889).