(+)-(R,Z)-5-Muscenone and (-)-(R)-Muscone by enantioselective aldol reaction and grob fragmentation

Chemistry - A European Journal

Volumn 16, Issue 8, 2010, Pages 2487-2495

  Fehr, Charles ^a   Buzas, Andrea K ^a   Knopff, Oliver ^a   De Saint Laumer, Jean Yves ^a  

^a Email:   (Switzerland)

Author keywords

Aldol reaction, amino alcohols, asymmetric synthesis, fragmentation, fragrances

Indexed keywords

ALDOL REACTIONS; AMINO ALCOHOLS; ASYMMETRIC SYNTHESIS; DIASTEREOSELECTIVE REDUCTION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; GROB FRAGMENTATION;

ALCOHOLS; AMINES; ELECTRON TRANSITIONS; ODORS;

SYNTHESIS (CHEMICAL);

EID: 77049128075     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902774     Document Type: Article

References (57)

1. E. Demole, C. Mahaim, P.-A. Blanc, EP 584477 to Firmenich (prior. 30. July 1992); Chem. Abstr. 1994, 120, 253 101.
2. C. Fehr, J. Galindo, O. Etter, Eur. J. Org. Chem. 2004, 1953.
3. O. Knopff, J. Kuhne, C. Fehr, Angew. Chem. 2007, 119, 1329;
4. Angew. Chem. Int. Ed. 2007, 46, 1307.
5. Review: C. Palomo, M. Oiarbide, J. M. Garcia, Chem. Soc. Rev. 2004, 33, 65.
6. (a) For examples with lanthanide/alkali metal complexes, see: M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187
7. b)With Zn-enolates: N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169;
8. B. M. Trost, H. Ito, E. R. Shilcoff, J. Am. Chem. Soc. 2001, 123, 3367
9. (c) With Ti enolates: R. Mahrwald, B. Ziemer, Tetrahedron Lett. 2002, 43, 4459.
10. (a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. Int. Ed. 1997, 36, 1237
11. (b) H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418 (footnote 11)
12. M. Inoue, N. Lee, S. Kasuya, T. Sato, M. Hirama, M. Moriyama, Y. Fukuyama, J. Org. Chem. 2007, 72, 3065.
13. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248
14. Angew. Chem. Int. Ed. 2004, 43, 5138
15. B. List, Tetrahedron 2002, 58, 5573
16. H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017
17. Angew. Chem. Int. Ed. 2004, 43, 1983 and references therein.
18. (a) L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 2002, 124, 10656
19. Z. G. Hayos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615
20. U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492
21. Angew. Chem. Int. Ed. 1971, 10, 496
22. see also: T. Nagamine, K. Inomata, Y. Endo, L. A. Paquette, J. Org. Chem. 2007, 72, 123
23. (b) J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7768;
24. Angew. Chem. Int. Ed. 2008, 47, 7656
25. see also: C. Agami, N. Platzer, H. Sevestre, Bull. Soc. Chim. Fr. 1987, 2, 358
26. (c) C. L. ChandlerB. List, J. Am. Chem. Soc. 2008, 130, 6737.
27. K. W. Henderson, W. J. Kerr, J. H. Moir, Synlett 2001, 1253.
28. For aldol reactions of Ti enolates, see: D. A. Evans, D. L. Rieger, M. T. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047;
29. Y. Tanabe, N. Matsumoto, T. Higashi, T. Misaki, T. Itoh, M. Yamamoto, K. Mitarai, Y. Nishii, Tetrahedron 2002, 58, 8269 and references therein.
30. N. Cabello, J.-C. Kizirian, S. Gille, A. Alexakis, G. Bernardinelli, L. Pinchard, J.-C. Caille, Eur. J. Org. Chem. 2005, 4835.
31. Preparation: (-)-27, NaH (1.2 equiv), THF, reflux, 45 min, then MeI (1.1 equiv), 45°C, 90 min (94% yield).
32. For most recent work, see: C. Fehr, H. Randall, Chem. Biodiversity 2008, 5, 942
33. C. Fehr, J. Galindo, I. Farris, A. Cuenca, Helv. Chim. Acta 2004, 87, 1737;
34. Angew. Chem. 1996, 108, 2726;
35. Angew. Chem. Int. Ed. 1996, 35, 2566.
36. 4 were all ineffective.
37. J.-C. Kizirian, J.-C. Caille, A. Alexakis, Tetrahedron Lett. 2003, 44, 8893;
38. Q. Perron, A. Alexakis, Tetrahedron: Asymmetry 2007, 18, 2503. We thank Prof. Alexakis for this valuable suggestion.
39. 4 (0 °C, 9 h) gave a conversion of approximately 20%.
40. H. Yamamoto, Tetrahedron 2007, 63, 8377.
41. D. E. Ward, M. Sales, P. K. Sasmal, J. Org. Chem. 2004, 69, 4808.
42. Subtle changes in the Ti reagent can greatly influence the diastereoselectivity, see: M. T. Crimmins, P. J. McDougall, Org. Lett. 2003, 5, 591
43. V. Rodriguez-Cisterna, C. Villar, P. Romea, F. Urpi, J. Org. Chem. 2007, 72, 6631
44. M. B. Hodge, H. F. Olivo, Tetrahedron 2004, 60, 9397.
45. P. S. Wharton, G. A. Hiegel, J. Org. Chem. 1965, 30, 3254
46. Review: D. Caine, Org. Prep. Proced. Int. 1988, 20, 1
47. a Early example: A. Eschenmoser, Helv. Chim. Acta 1952, 35, 1660.
48. For another stereodivergent reduction/fragmentation, in which a 3-hydroxy ketone is converted into either a Z- or an E-unsaturated macrocyclic ketone, see: C. Fehr, J. Galindo, O. Etter, W. Thommen, Angew. Chem. 2002, 114, 4705;
49. Angew. Chem. Int. Ed. 2002, 41, 4523.
50. D. A. Evans, A. H. Hoveyda, J. Org. Chem. 1990, 55, 5190
51. D. A. Evans, D. A. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560.
52. H. C. Brown, S. Krishnamurthy, J. Am. Chem. Soc. 1972, 94, 7159.
53. For 1,2-hydride shifts with concomitant departure of bromide, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 725.
54. -1, respectively. These values should be only considered qualitatively, as the reactive species are different (OK instead of OH, OTs instead of OMe).
55. J. Saavedra, J. Org. Chem. 1985, 50, 2271.
56. P. C. B. Page, H. Heaney, S. Reignier, G. A. Rassias, Synlett 2003, 22.
57. K. Soai, S. Yokoyama, T. Hayasaka, J. Org. Chem. 1991, 56, 4264.