Catalytic asymmetric conjugate reduction with ethanol: A more reactive system Pd(II)-iPr-DUPHOS complex with molecular sieves 4A

Journal of Organometallic Chemistry

Volumn 693, Issue 5, 2008, Pages 867-873

  Monguchi, Daiki ^a   Beemelmanns, Christine ^a   Hashizume, Daisuke ^a   Hamashima, Yoshitaka ^a   Sodeoka, Mikiko ^a  

^a RIKEN   (Japan)

Author keywords

Asymmetric catalysis; Conjugate reduction; DUPHOS; Ethanol; Molecular sieves 4A; Palladium

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; ETHANOL; MOLECULAR SIEVES; SOLVENTS;

CARBONYL COMPOUNDS; CONJUGATE REDUCTION; X-RAY STRUCTURAL ANALYSIS;

PALLADIUM;

EID: 38949167538     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.10.005     Document Type: Article

References (34)

1. Cu: esters. Appella H.D., Moritani Y., Shintani R., Ferreria M.E., and Buchwald L.S. J. Am. Chem. Soc. 121 (1999) 9473
2. Hughes G., Kimura M., and Buchwald L.S. J. Am. Chem. Soc. 125 (2003) 11253
3. Lipshutz H.B., Servesko M.J., and Taft R.B. J. Am. Chem. Soc. 126 (2004) 8352
4. nitroolefins. Czekelius C., and Carreira M.E. Angew Chem., Int. Ed. 42 (2003) 4793
5. enones. Moritani Y., Appella H.D., Jurkauskas V., and Buchwald L.S. J. Am. Chem. Soc. 122 (2000) 6797
6. Lipshutz H.B., and Servesko M.J. Angew. Chem., Int. Ed. 42 (2003) 4789
7. Lipshutz H.B., Servesko M.J., Petersen B.T., Papa P.P., and Lover A.A. Org. Lett. 6 (2004) 1273
8. Lipshutz H.B., Frieman A.B., and Tomaso Jr. E.A. Angew. Chem., Int. Ed. 45 (2006) 1259
9. unsaturated sulfones. Llamas T., Arrayás R.G., and Carretero J.C. Angew. Chem., Int. Ed. 46 (2007) 3329
10. Desrosiers J.-N., and Charette A.B. Angew. Chem., Int. Ed. 46 (2007) 5955
11. acrylonitriles. Lee D., Yang Y., and Yun J. Org. Lett. 9 (2007) 2749
12. Rh: esters. Tsuchiya Y., Kanazawa Y., Shiomi T., Kobayashi K., and Nishiyama H. Synlett (2004) 2493
13. enones. Kanazawa Y., Tsuchiya Y., Kobayashi K., Shiomi T., Itoh J., Kikuchi M., Yamamoto Y., and Nishiyama H. Chem. Eur. J. 12 (2006) 63
14. aldehydes. Kanazawa Y., and Nishiyama H. Synlett (2006) 3343
15. 4. Leutenegger U., Madin A., and Pfaltz A. Angew. Chem., Int. Ed. 28 (1989) 60
16. Ohtsuka Y., Ikeno T., and Yamada T. Tetrahedron Asymm. 14 (2003) 967
17. Geiger C., Kreimeier P., and Reiser O. Adv. Synth. Catal. 347 (2005) 249
18. Organocatalysis. Tang W.J., Fonseca H.T.M., Vignola N., and List B. Angew. Chem., Int. Ed. 44 (2005) 108
19. Ouellet G.S., Tuttle B.M., and Macmillan C.W.D. J. Am. Chem. Soc. 127 (2005) 32
20. Tuttle J.B., Ouellet S.G., and MacMillan D.M.C. J. Am. Chem. Soc. 128 (2006) 12662
21. Martin N.J.A., and List B. J. Am. Chem. Soc. 128 (2006) 13368
22. Tsuchiya Y., Hamashima Y., and Sodeoka M. Org. Lett. 8 (2006) 4851
23. Other reactions using 1a and 2a. Fujii A., Hagiwara E., and Sodeoka M. J. Am. Chem. Soc. 121 (1999) 5450
24. Hamashima Y., Hotta D., and Sodeoka M. J. Am. Chem. Soc. 124 (2002) 11240
25. Hamashima Y., Yagi K., Takano H., Tamás L., and Sodeoka M. J. Am. Chem. Soc. 124 (2002) 14530
26. Hamashima Y., Suzuki T., Takano H., Shimura Y., and Sodeoka M. J. Am. Chem. Soc. 127 (2005) 10164
27. Sasamoto N., Dubs C., Hamashima Y., and Sodeoka M. J. Am. Chem. Soc. 128 (2006) 14010
28. Sodeoka M., and Hamashima Y. Pure Appl. Chem. 78 (2006) 477
29. Selected examples of Pd(II)-DUPHOS complexes. Brunker T.J., Blank N.F., Moncarz J.R., Scriban C., Anderson B.J., Glueck D.S., Zakharov L.N., Golen J.A., Sommer R.D., Incarvito C.D., and Rheingold A.L. Organometallics 24 (2005) 2730
30. Blank N.F., Moncarz J.R., Brunker T.J., Scriban C., Anderson B.J., Amir O., Glueck D.S., Zakharov L.N., Golen J.A., Incarvito C.D., and Rheingold A.L. J. Am. Chem. Soc. 129 (2007) 6847
31. Gini F., Hanssen B., and Minnaard A.J. Org. Lett. 7 (2005) 5309
32. Miyaura et al. discussed in their paper the enantioselection mechanism in their Pd-catalyzed conjugate addition of aryl metal reagents using calculated catalyst-substrate models similar to the model shown in Scheme 4. Nishikata T., Yamamoto Y., Gridnev I.D., Miyaura N. Organometallics 24 (2005) 5025
33. Yamamoto Y., Nishikata T., and Miyaura N. J. Synth. Org. Chem., Jpn. (2006) 1112
34. 2OD was used as a solvent. This indicates that the final protonation step is a rate determining step. Details of these kinetic studies will be reported elsewhere.