Catalytic diastereoselective reductive aldol reaction: Optimization of interdependent reaction variables by arrayed catalyst evaluation [10]

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 12202-12203

  Taylor, Steven J ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; LIGAND; METAL;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033616095     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992952e     Document Type: Letter

References (41)

1. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
2. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
3. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
4. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
5. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
6. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
7. For lead references in regards to enantioselective catalysis, see: Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357. For catalytic diastereoselective processes, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. For recent work not covered in these references, see: (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (c) Evans, D. A.; Kozlowski, M. C.; Murray, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (e) Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1999, 71.
8. (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
9. (b) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005.
10. (c) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. For a reductive aldol reaction with unsaturated ketones, see: Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331.
11. (c) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. For a reductive aldol reaction with unsaturated ketones, see: Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331.
12. For group 9 and group 10 transition metal-catalyzed aldol reactions of silyl enol ethers, see: (a) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
13. (b) Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793.
14. (c) Slough, G. A.; Bergman, R. G.; Heatchcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
15. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
16. (e) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
17. (f) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032.
18. For related catalytic, reductive condensation between alkenes or alkynes and carbonyls, see: (a) Ojima, I.; Tzamarioudaki, M.; Tsai, C.-Y. J. Am. Chem. Soc. 1994, 116, 3643.
19. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
20. (c) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785.
21. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
22. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
23. (f) Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
24. (g) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
25. (h) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
26. (i) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098. For catalyzed and noncatalyzed two- step sequential acrylate reduction-aldol addition, see: Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5678. Boldrini, G. P.; Bortolotti, M.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 5820.
27. (i) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098. For catalyzed and noncatalyzed two-step sequential acrylate reduction-aldol addition, see: Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5678. Boldrini, G. P.; Bortolotti, M.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 5820.
28. (i) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098. For catalyzed and noncatalyzed two- step sequential acrylate reduction-aldol addition, see: Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5678. Boldrini, G. P.; Bortolotti, M.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 5820.
29. For recent reviews of high-throughput and combinatorial approaches to catalyst development, see: (a) Bein, T. Angew. Chem., Int. Ed. 1999, 38, 323.
30. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
31. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Op. Chem. Biol. 1998, 2, 422.
32. (d) Weinberg, W. H.; Jandeleit, B.; Self, K.; Turner, H. Cur. Op. Solid State Mater. Sci. 1998, 3, 104.
33. For catalyst lead discovery, as opposed to optimization, with combinatorial chemistry, see: Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937.
34. For a fractional factorial approach to multivariant optimization of organometallic reactions, see: Schwindt, M. A.; Lejon, T.; Hegedus, L. S. Organometallics 1990, 9, 2814.
35. For a review of transition metal-catalyzed hydroboration, see: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957-5026. For transition metal- catalyzed hydrosilation, see: Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993; Chapter 6.
36. For a review of transition metal-catalyzed hydroboration, see: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957-5026. For transition metal-catalyzed hydrosilation, see: Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993; Chapter 6.
37. iPr-pybox, 2,6-bis(4-isopropyl-2-ozazolin-2-yl)pyridine-binap; tBu-box, 2,2′-isopropylidenebis(4-tert-butyl-2-oxazoline); Ph-semicorrin, 4-phenyl-α-[4-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile; MOP, 2-(diphenylphosphino-2′methoxy-1,1′-binaphthyl; BINAP, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; DUPHOS, 1,2-bis(2,5)-dimethylphospholano)-benzene; QUINAP, 1-(2-diphenylphospino-1-naphthyl)isoquinoline.
38. 3SiH (5.8:1 syn:anti). See Supporting Information for selectivity of all reactions.
39. While we have no experimental evidence in regards to reaction mechanism, it is plausible that insertion of the acrylate alkene into a metal hydride provides a metal enolate. It is known that similar rhodium enolates will add to nonenolizable aldehydes in an aldol fashion hut are protonated by aldehydes hearing an α-hydrogen (ref 3c). This may offer an explanation for diminished product yield with isobutyraldehyde.
40. 2MeSiH reproducibly provides 23:1 syn:anti selectivity in a 96-well plate at 0.2 M substrate concentration. In general, reactions in the 96-well plate format proceed without noticeable loss in reaction volume over the course of the experiment.
41. Enantioselective transformation was observed with a few of the catalyst systems described in Figure I. Further discussion at this point is unwarranted as ee values were lower than 30%.