A practical synthesis of optically active α-substituted ketones in high enantiomeric excess

Synthesis

Volumn , Issue 4, 2007, Pages 638-641

  Soorukram, Darunee ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Allylic substitution; Chiral substituted ketones; Organocopper; Organozinc

Indexed keywords

ALLYLIC SUBSTITUTION; CHIRAL SUBSTITUTED KETONES; ORGANOCOPPER; ORGANOZINC;

ENANTIOMERS; OPTICAL PROPERTIES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KETONES;

1 IDO 5,5 DINETHYL 6 PENTYLCYCLOHEX 1 ENE; 1 IODO 5 METHYL 5 PENTYLCYCLOPENT 1 ENE; 1 IODO 5 PENTYLCYCLOPENT 1 ENE; 2 CYCLOHEXYLCYCLOHEPTANONE; 2 METHYL 2 PENTYLCYCLOPENTANONE; 2 PENTYLCYCLOPENTANONE; 3,3 DIMETHYL 2 PENTYLCYCLOHEXANONE; 7 CYCLOHEXYL 1 IODOCYCLOHEPT 1 ENEN; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33947540327     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965887     Document Type: Article

References (48)

1. (a) Fey, P.; Hartwig, W. In Stereoselective Synthesis, Vol 2; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: Stuttgart, 1996, 969.
2. (b) Fey, P.; Hartwig, W. In Stereoselective Synthesis, Vol 2; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: Stuttgart, 1996, 994.
3. (c) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4413.
4. (d) Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1337.
5. (e) Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1362.
6. (f) Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 62.
7. (g) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192.
8. (h) Liao, S.; Collum, D. B. J. Am. Chem. Soc. 2003, 125, 15114.
9. (i) Job, A.; Janeck, C F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
10. (j) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
11. (k) Nakamura, M.; Hatakeyama, T.; Hara, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 6362.
12. (l) Hirata, T.; Shimoda, K.; Kawano, T. Tetrahedron: Asymmetry 2000, 11, 1063.
13. (m) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takata, S. J. Org. Chem. 1995, 60, 357.
14. (n) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809.
15. (a) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657.
16. (b) Sonnet, P. E.; Heath, R. R. J. Org. Chem. 1980, 45, 3137.
17. (c) Evans, D. A.; Takacs, J. M. Tetrahedron Lett. 1980, 21, 4233.
18. (d) Helmchen, G.; Weirchowski, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 60.
19. (e) Enders, D.; Eichenauer, H.; Baus, U.; Schubert, H.; Kremer, K. A. M. Tetrahedron 1984, 40, 1345.
20. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
21. (a) Evans, D. A. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: New York, 1984, 1; and references cited therein,
22. (b) d'Angelo, J. Tetrahedron 1976, 32, 2979.
23. (c) Caine, D. In Carbon-Carbon Bond Formation, Vol. 1; Augustine, R. L., Ed.; Marcel Dekker: New York, 1979, 85.
24. (d) Pollack, R. M. Tetrahedron 1989, 45, 4913; and references cited therein.
25. (e) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin/Cummings: Menlo Park, California, 1972, Chap. 9, 492.
26. (f) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part B: Reactions and Synthesis, 2nd ed.; Plenum Press: New York, 1983, Chap. 1, 1.
27. (a) Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111.
28. (b) Calaza, M. I.; Hupe, E.; Knochel, P. Org. Lett. 2003, 5, 1059.
29. (c) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147.
30. (d) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem. Int. Ed. 2004, 43, 2426.
31. (e) Alexakis, A.; Polet, D. Org. Lett. 2004, 6, 3529.
32. (f) Tissot-Croset, K.; Alexakis, A. Tetrahedron Lett. 2004, 45, 7375.
33. (g) Alexakis, A.; Tomassini, A.; Andrey, O.; Bernardinelli, G. Eur. J. Org. Chem. 2005, 1332.
34. (h) Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621.
35. (i) Leuser, H.; Perrone, S.; Liron, F.; Kneisel, F. F.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44, 4627.
36. (j) Breit, B.; Demel, P.; Studte, C. Angew. Chem. Int. Ed. 2004, 43, 3785.
37. (k) Breit, B.; Herber, C. Angew. Chem. Int. Ed. 2004, 43, 3790.
38. Soorukram, D.; Knochel, P. Org. Lett. 2004, 6, 2409.
39. Soorukram, D.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 3686.
40. For the preparation of α-chiral ketones by other methods, see for example: (a) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. J. Am. Chem. Soc. 1981, 103, 3081.
41. (b) Meyers, A. I.; Williams, D. R.; White, S.; Erickson, G. W. J. Am. Chem. Soc. 1981, 103, 3088; see also references 1, 2 and 4 cited therein.
42. (a) Bauer, K.; Garbe, D.; Suburg, H. Common Fragrance and Flavor Materials; Wiley-VCH: Weinheim, 1997.
43. (b) Corma, A.; Iborra, S.; Mifsud, M.; Renz, M.; Susarte, M. Adv. Synth. Catal. 2004, 346, 257.
44. (a) Knochel, P.; Millot, N.; Rodriguez, A. L. Org. React. 2001, 58, 417.
45. (b) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1988, 29, 2395.
46. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
47. (d) Knochel, P.; Jones, P. Organozinc Reagents. A Practical Approach; Oxford University Press: Oxford, 1999.
48. (e) Rao, S. A.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 5735.