Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess

Tetrahedron

Volumn 53, Issue 3, 1997, Pages 1015-1024

  Markó, István E ^a   Giles, Paul R ^a   Hindley, Nigel J ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; ALKENE DERIVATIVE; AMINOALCOHOL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031032230     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01001-0     Document Type: Article

References (39)

1. Zeneca Research Fellow 1994-1997. Recipient of the Merck Young Investigator Award 1995.
2. Part of this work was performed at the University of Sheffield, Sheffield S3 7HF, U.K.
3. (a) Drewes, S.E.; Roos, G.H.P. Tetrahedron, 1988, 44, 4653.
4. (b) Hoffmann, H.M.R.; Rabe, J. Angew Chem., Int. Ed. Engl., 1985, 24, 94.
5. Basavaiah, D.; Rao, P.D.; Hyma, R.S. Tetrahedron, 1996, 52, 8001.
6. (a) Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron, 1992,48, 6371 and references cited therein.
7. (b) Hill, J.S.; Isaacs, N.S. J. Phys. Org. Chem., 1990, 3, 285.
8. (c) Hoffmann, H.M.R.; Rabe, J. Angew. Chem., Int. Ed. Engl., 1983, 22, 795.
9. Bailey, M.; Markó, I.E.; Ollis, W.D. Tetrahedron Lett., 1991, 32, 2687.
10. Bailey, M.; Markó, I.E.; Ollis, W.D. Tetrahedron Lett., 1990, 31, 4509.
11. (a) Bailey, M.; Staton, I.; Ashton, P.R.; Markó, I.E.; Ollis, W.D. Tetrahedron Asymmetry, 1991, 2, 495.
12. (b) Markó, I.E. in: Organometallic Reagents in Organic Synthesis, Bateson, J.H.; Mitchell, M.B. Eds. Academic Press., London, 1994, p. 34.
13. For kinetic resolutions using enzymes or microorganisms, see: (a) Burgess, K.; Jennings, L.D. J. Org. Chem., 1990,55, 1138.
14. (b) Basavaiah, D.; Dharma Rao, P. Synth. Commun., 1994,24, 917.
15. (c) Adam, W.; Hoch, U.; Saha-Moller, C.R.; Schreier, P. Angew. Chem., Int. Ed. Engl., 1993,32, 1737.
16. For kinetic resolution using asymmetric hydrogenation, see: (a) Brown, J.M. Angew. Chem., Int. Ed. Engl., 1987, 26, 190.
17. (b) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem., 1988, 53, 708.
18. Diastereocontrolled Baylis-Hillman reactions have been reported earlier: (a) Brown, J.M.; Cutting, L; Evans, P.L., Maddox, P.J. Tetrahedron Lett., 1986,27, 3307.
19. (b) Basavaiah, D.; Gowriswari, V.V.L.; Sarma, P.K.S., Dharma Rao, P. Tetrahedron Lett., 1990,31, 1621.
20. (c) Drewes, S.E.; Emslie, N.D.; Field, J.S.; Khan, A.A.; Ramesar, N. Tetrahedron Lett, 1993,34, 1205.
21. (d) Drewes, S.E.; Emslie, N.D.; Khan, A.A. Synth. Commun., 1993, 23, 1215.
22. For Baylis-Hillman condensations using chiral aldehydes, see (a) Drewes, S.E.; Manickum, T.; Roos, G.H.P. Synth Commun, 1988, 18, 1065.
23. (b) Drewes, S.E.; Khan, A.A.; Rowland, K. Synth Commun, 1993, 23, 183
24. (c) Kundig, E.P.; Xu, L.H.; Romanens, P.; Bernadinelli, G. Tetrahedron Lett., 1993,34, 7049.
25. A number of diastereoselective routes have been described using chiral auxiliaires attached on the acrylate moiety or employing optically active aldehydes (ref. 3a). In his seminal review, Drewes mentions the use of chiral amines to catalyse the asymmetric Baylis-Hillman reaction. However, both the yields and the enantiomeric excesses are low (< 10%).
26. Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron Asymmetry, 1995, 6, 1241.
27. Barrett, A.G.M.; Kamimura, A. J. Chem. Soc., Chem. Commun., 1995, 1755. For kinetic resolution using the Sharpless epoxidation protocol, see : Markó, I.E. refs. 5, 7a and 7b. For a recent use of our technique, see : Hirama, M. ref. 10.
28. (a) Drewes, S.E.; Freese, S.D.; Emslie, N.D.; Roos, G.H.P. Synth. Commun., 1988, 18, 1565.
29. (b) Bailey, M.; Markó, I.E.; Ollis, W.D.; Rassmussen, P.R. Tetrahedron Lett, 1990, 31, 4509.
30. Bailey, M. Ph.D. Thesis, 1991, University of Sheffield, Sheffield, UK. The use of AcOH as cocatalyst was described earlier: Hoffmann, H.M.R. J. Org. Chem., 1988, 53, 3701.
31. Bailey, M. Ph.D. Thesis, 1991, University of Sheffield, Sheffield, UK. The use of AcOH as cocatalyst was described earlier: Hoffmann, H.M.R. J. Org. Chem., 1988, 53, 3701.
32. For an excellent monograph on high pressure techniques, see : Organic Synthesis at High Pressures, Matsumoto, K.; Acheson, R.M., J. Wiley, 1991. The promotion of Baylis-Hillman reactions by high-pressure has been reported earlier: Gilbert, A.; Heritage, T.W.; Isaacs, N.S.; Tetrahedron Asymmetry, 1991, 2, 969.
33. For an excellent monograph on high pressure techniques, see : Organic Synthesis at High Pressures, Matsumoto, K.; Acheson, R.M., J. Wiley, 1991. The promotion of Baylis-Hillman reactions by high-pressure has been reported earlier: Gilbert, A.; Heritage, T.W.; Isaacs, N.S.; Tetrahedron Asymmetry, 1991, 2, 969.
34. This discrepancy in e.e. is due to quinine and quinidine being "pseudo-enantiomers" and not true enantiomers. For related observations, see for example : Jacobsen, E.N.; Markó, I.E.; Mungall, W.S.; Schröder, G.; Sharpless, K.B. J. Am. Chem. Soc., 1988,110, 1968 and references cited therein.
35. (a) Bode, M.L.; Kaye, P.T. Tetrahedron Lett., 1991, 32, 5611.
36. (b) Drewes, S.E.; Njamala, O.L.; Emslie, N.D.; Ramesar, N.; Field, J.S. Synth. Commun., 1993,23, 2807.
37. (c) Ameer, F.; Drewes, S.E.; Freese, S.; Kaye, P.T. Synth. Commun., 1988,18, 495.
38. (d) Basavaiah, D.; Sarma, P.K.S. Synth. Commun., 1990,20, 1611.
39. When optically enriched BH adduct 21 (R=Cy) was resubjected to the reaction conditions (10 Kbars, 3 days), the e.e. decreased to about 10% e.e.. However, the yield of 21 was also much lower. We are grateful to a Referee to suggest this experiment.