A high-throughput screening approach for the determination of additive effects in organozinc addition reactions to aldehydes

Advanced Synthesis and Catalysis

Volumn 347, Issue 10, 2005, Pages 1361-1368

  Rudolph, Jens ^b,c   Lormann, Matthias ^a   Bolm, Carsten ^b   Dahmen, Stefan ^a  

^a CYNORA GMBH   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c BASF SE   (Germany)

Author keywords

Additives; Asymmetric catalysis; Combinatorial catalysis; High throughput screening; Organozinc reagents

Indexed keywords

EID: 24644450204     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505090     Document Type: Article

References (51)

1. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
2. b) Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
3. c) Catalytic Asymmetric Synthesis, 2nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000;
4. d) Transition Metals for Organic Synthesis, 2nd edn., (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004;
5. e) for recent advances, see: Enantioselective Catalysis, (Eds.: C. Bolm, J. Gladysz), Chem. Rev. 2003, 103, 276;
6. f) H. Tye, P. J. Comina, J. Chem. Soc. Perkin Trans. 1 2001, 1729.
7. a) Transition State Modelling for Catalysis, (Eds.: D. G. Truhlar, K. Morokuma), ACS Symposium Series 721, Washington DC, 1999;
8. b) Computational Organometallic Chemistry, (Ed.: T. R. Cundari), Marcel Dekker, Basel, 2001;
9. c) M. Torrent, M. Solà, G. Frenking, Chem. Rev. 2000, 100, 439.
10. 2O: S. Ribe, P. Wipf, Chem. Commun. 2001, 299;
11. b) MeOH: P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444;
12. c) for a review on additive effects in catalyses: E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 1570;
13. d) for a review on halide effects, see: K. Fagnou, M. Lautens, Angew. Chem. Int. Ed. 2002, 41, 26.
14. H. U. Blaser, Adv. Synth. Catal. 2002, 344, 17.
15. Selected reviews: a) M. T. Reetz, Angew. Chem. Int. Ed. 2001, 40, 312;
16. b) S. Dahmen, S. Bräse, Synthesis 2001, 10, 1431;
17. c) M. T. Reetz, Angew. Chem. Int. Ed. 2002, 41, 1335;
18. d) J. G. de Vries, A. H. M. de Vries, Eur. J. Org. Chem. 2003, 799.
19. a) L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757;
20. [1b] p. 911;
21. c) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833;
22. d) R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49;
23. e) D. A. Evans, Science 1988, 240, 420.
24. For examples, see: a) C. A. Parrodi, E. Juaristi, L. Quintero- Cortés, P. Amador, Tetrahedron: Asymmetry 1996, 7, 1915;
25. b) D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 1997, 8, 2479.
26. In our scenario, the pathway leading to a racemic product is catalyzed, too, but not in a stereoselective manner. We therefore used the term "uncatalyzed" for the undirected pathway.
27. a) C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850;
28. b) J. Rudolph, N. Hermanns, C. Bolm, J. Org. Chem. 2004, 69, 3997;
29. c) S. Dahmen, Org. Lett. 2004, 6, 2113;
30. d) J. Rudolph, F. Schmidt, C. Bolm, Synthesis 2005, 840;
31. e) for a study on the use of PEG-supported ferrocene in the phenyl transfer reaction, see: C. Bolm, N. Hermanns, A. Claßen, K. Muñiz, Bioorg. Med. Chem. Lett. 2002, 12, 1795.
32. a) J. Rudolph, F. Schmidt, C. Bolm, Adv. Synth. Catal. 2004, 346, 867;
33. b) C. Bolm, L. Zani, J. Rudolph, I. Schiffers, Synthesis 2004, 2173;
34. c) C. Bolm, F. Schmidt, L. Zani, Tetrahedron: Asymmetry 2005, 16, 1367.
35. a) C. Bolm, N. Hermanns, J. P. Hildebrand, K. Muñiz, Angew. Chem. Int. Ed. 2000, 39, 3465;
36. b) C. Bolm, M. Kesselgruber, N. Hermanns, J. P. Hildebrand, Angew. Chem. Int. Ed. 2001, 40, 1488;
37. c) C. Bolm, M. Kesselgruber, A. Grenz, N. Hermanns, J. P. Hildebrand, New J. Chem. 2001, 25, 13;
38. d) C. Bolm, N. Hermanns, M. Kesselgruber, J. P. Hildebrand, J. Organomet. Chem. 2001, 624, 157.
39. [15a]
40. and b) J.-X. Ji, J. Wu, T. T.-L. Au-Yeung, C.-W. Yip, R. K. Haynes, A. S. C. Chan, J. Org. Chem. 2005, 70, 1093;
41. c) D.-H- Ko, K. H. Kim, D.-C. Ha, Org. Lett. 2002, 4, 3759.
42. 2-Bromobenzaldehyde was chosen because the addition product gives a good HPLC resolution using a Chiral-cel-OD phase, with short retention times for the two enantiomers. Additionally it is a rather difficult substrate, thus allowing space for improvement. As shown in previous studies, the enantioselectivities for other ortho-substituted aromatic substrates are comparable.
43. P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444.
44. a) M. Fontes, X. Verdagner, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 2532;
45. b) N. Hermanns, PhD thesis, RWTH Aachen University, Germany, 2002;
46. c) J. Rudolph, PhD thesis, RWTH Aachen University, Germany, 2005.
47. [9b]) and might be correlated to the chosen substrate or catalyst.
48. Commercially available diethylzinc solution can contain considerable amounts of zinc salts. Usually their effect becomes only apparent, when highly active zinc reagents such as phenylzincs or alkynylzincs are used.
49. For the transition state description of the phenyl transfer to aldehydes, see: a) J. Rudolph, T. Rasmussen, C. Bolm, P.-O. Norrby, Angew. Chem. Int. Ed. 2003, 42, 3002;
50. b) J. Rudolph, P.-O. Norrby, C. Bolm, J. Am. Chem. Soc. 2005, 127, 1548.
51. 3/diethylzinc protocol. In the diethylzinc addition to aldehydes no effect of imidazole was observed. In this reaction, imidazole does not seem to be deprotonated by diethylzinc. Hence formation of a mixed imidazolyl-aryl-zinc reagent can only be achieved by the more basic phenylzinc.