Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2253-2256

  Guz, Nathan R ^a   Phillips, Andrew J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; BIOLOGICAL FACTOR; OXAZOLE DERIVATIVE; OXAZOLIDINE; SPARTEINE; THIOKETONE; TITANIUM; TITANIUM TETRACHLORIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; BIOLOGICAL FACTORS; OXAZOLES; SPARTEINE; STEREOISOMERISM; THIONES; TITANIUM;

EID: 0037182708     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026108w     Document Type: Article

References (50)

1. For selected reviews see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
2. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917.
3. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
4. (d) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
5. (a) For a review see: Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 59, 1353.
6. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
7. (c) Keck, G. E.; Kishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363.
8. (d) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742.
9. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
10. Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586.
11. For a review of acetate aldol reactions, see: M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For more recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (a) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439.
12. (b) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874.
13. (c) Yan, T. H.; Hung, H. C.; Hung, A. W.; Lee, H. C.; Chang, C. S. J. Org. Chem. 1994, 59, 8187.
14. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397.
15. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180.
16. (f) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378. For approaches utilizing metal-based chirality, see
17. (g) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279.
18. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495.
19. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
20. (a) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031.
21. (b) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397 and references therein.
22. Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418. For reactions of Sn(II) enolates of 5-substituted thiazolidinethiones with α,β-unsaturated aldehydes, see: Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391.
23. Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418. For reactions of Sn(II) enolates of 5-substituted thiazolidinethiones with α,β-unsaturated aldehydes, see: Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391.
24. The dibutylboryl enolate of Evans' valine-derived oxazolidinone gives a 52:48 ratio of diastereoisomers with isobutyraldehyde and a 72:28 ratio with acetaldehyde (see ref 3).
25. Recent studies from the Yan and Crimmins groups have shown that oxazolidinethiones are valuable auxiliaries for syn propionate aldol additions, particularly when employed as their Ti(IV) enolates; see: (a) Yan, T. H.; Tan, C. W.; Lee, H. C.; Lo, H. C.; Huang, T. Y. J. Am. Chem. Soc. 1993, 115, 2613.
26. (b) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
27. (c) Crimmins, M. T.; King, B. W. J. Am. Chem. Soc. 1998, 120, 9084.
28. (d) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
29. Related heterocyclcs such as (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one ("SuperQuat") have been studied by Davies in the context of conjugate additions and alkylation reactions. For a recent paper, see: Bull, S. D.; Davies, S. G.; Nicholson, R. L.; Sanganee, H. J.; Smith, A. D. Tetrahedron: Asymmetry 2000, 11, 3475 and references therein.
30. For two relevant examples of acetate aldol reactions with titanium enolates of thiazolidinethiones, see: (a) González, A.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
31. (b) Crimmins, M. T.; Emmitte, K. A. Org. Lett. 1999, 1, 2029.
32. Seebach has reported the synthesis of the corresponding oxazolidinone. Suprisingly, it exhibited only modest diastereoselectivity for acetate aldol reactions; see: Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093.
33. (a) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Chem. Commun. 1983, 469.
34. (b) Delaunay, D.; Toupet, L. Corre, M. L. J. Org. Chem. 1995, 60, 6604.
35. The corresponding Li and B enolates gave poor conversion and diastereoselectivity.
36. Guz, N. R.; Phillips, A. J. Unpublished results. Repeat reactions with hexanal gave dr values of 95.3:4.7, 95.7:4.3, and 94.6:5.4.
37. 3). See: Harada, T.; Kurokawa, H.; Kagamihara, Y.; Tanaka, S.; Inoue, A. J. Org. Chem. 1992, 57, 1412.
38. 3). See: Harada, T.; Kurokawa, H.; Kagamihara, Y.; Tanaka, S.; Inoue, A. J. Org. Chem. 1992, 57, 1412.
39. 4 and trialkylamine bases (see ref 9a), and for titanium enolates of thiazolidinethiones generated with trialkylamine bases (Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775). For related aldol reactions with N-acyl oxazolidineselones that presumably react via the same transition state, see: Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A., III J. Am. Chem. Soc. 2000, 122, 386.
40. 4 and trialkylamine bases (see ref 9a), and for titanium enolates of thiazolidinethiones generated with trialkylamine bases (Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775). For related aldol reactions with N-acyl oxazolidineselones that presumably react via the same transition state, see: (c) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A., III J. Am. Chem. Soc. 2000, 122, 386.
41. 4 and trialkylamine bases (see ref 9a), and for titanium enolates of thiazolidinethiones generated with trialkylamine bases (Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775). For related aldol reactions with N-acyl oxazolidineselones that presumably react via the same transition state, see: Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A., III J. Am. Chem. Soc. 2000, 122, 386.
42. Crimmins has observed that oxazolidinethiones without substituents at C5 require a second equivalent of titanium to produce "non-Evans" syn adducts (ref 9b,d). In contrast, Yan's camphor-based oxazolidinethiones and oxazolidinones react with opposite facial selectivity in the presence of only 1 equiv of titanium (ref 9a).
43. Guz, N. R.; Phillips, A. J. Unpublished results. The observed facial selectivity is the same as that observed for the oxazolidinethione.
44. The calculation of transition structures and energies for these reactions is complicated by uncertainty with respect to the ligand sphere around titanium. We have chosen to depict B as the tetrachlorotitanium species on the basis of speculations first advanced by Evans; see (a) Evans, D. A.; Urpí, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8214.
45. (b) Bilodeau, M. T. Ph.D. Thesis, Harvard University, 1994.
46. (a) Li, Y.; Paddon Row: M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481.
47. (b) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
48. (a) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
49. (b) Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.
50. We have calculated the dipole moments (MP2, 6-31G*) for oxazolidinone (5.40 D, lit. 5.07 D Lee, C. M.; Kumler, W. D. J. Am. Chem. Soc. 1961, 83, 4596) and oxazolidinethione (6.86 D). These values suggest that the rotameric populations around the enolate-auxiliary bond may be different for each system. Calculations were performed using PC Spartan Pro, Wavefunction Inc., Irvine, CA.