Efficient enantioselective synthesis of methyl esters of α-unsubstituted β-hydroxy acids via asymmetric aldol-type addition of chiral boron enolates of (methylthio)acetic acid to aldehydes

Synthesis

Volumn , Issue 10, 1996, Pages 1207-1211

  Fringuelli, Francesco ^a   Piermatti, Oriana ^a   Pizzo, Ferdinando ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029847678     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4365     Document Type: Article

References (60)

1. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
2. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
3. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
4. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
5. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
6. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
7. For recent literature on achiral boron enolates of methylene-active compounds, see the following references and those cited therein: (a) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716. (c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767. (d) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147. (e) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162. (f) Ganesan, K.; Brown, H. C J. Org. Chem. 1994, 59, 2336. (g) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
8. (a) Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566.
9. (b) Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett. 1986, 27, 4748.
10. (c) Reetz, M. T.; Kunish, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721.
11. Enders, D.; Lohray, B. B. Angew. Chem. Int. Ed. Engl. 1988, 27, 581.
12. (e) Goodman, J. M.; Kahn, D.; Paterson, I. J. Org. Chem. 1990, 55, 3295.
13. (f) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norkross, R. D. Tetrahedron 1990, 46, 4663.
14. (g) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
15. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
16. (i) Gennari, C.; Moresca, D.; Vulpetti, A.; Pain, G. Tetrahedron Lett. 1994, 35, 4623.
17. (a) Fringuelli, F.; Martinetti, E.; Piermatti, O.; Pizzo, F. Gazz. Chim. Ital. 1993, 123, 637.
18. (b) Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1995, 60, 7006.
19. (a) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365.
20. (b) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276.
21. (c) Corey, E. J.; Choi, S. Tetrahedron Lett. 1991, 32, 2857.
22. (d) Kiyooka, S.; Kaneko, Y.; Kume, K. Tetrahedron Lett. 1992, 33, 4927.
23. (e) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Scappini, A. M. Gazz. Chim. Ital. 1995, 125, 195.
24. (a) Masamune, S.; Sato, T.; Kim, B. M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279.
25. (b) Corey, E. J.; Lee, D.-H. Tetrahedron Lett 1993, 34, 1737.
26. (c) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem. 1993, 105, 1717; Angew. Chem. Int. Ed. Engl. 1993, 32, 1618.
27. (c) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem. 1993, 105, 1717; Angew. Chem. Int. Ed. Engl. 1993, 32, 1618.
28. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
29. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
30. (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767.
31. (d) Draws, S. E.; Malissar, D. G. S.; Ross, G. H. P. Tetrahedron: Asymmetry 1992, 3, 515.
32. (e) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439.
33. (f) Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321.
34. (g) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187.
35. (h) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.; Liu, W.-H. J. Org. Chem. 1995, 60, 3301.
36. (a) Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278.
37. (b) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309.
38. (a) Masamune, S.; Taiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521.
39. (b) Masamune, S.; Lu, L. D.-L.; Jackson, W. P.; Kaiho, T.; Toyoda, T. J. Am. Chem. Soc. 1982, 104, 5523.
40. (c) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528.
41. (d) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569.
42. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729.
43. (b) Deloux, Srebnik, M. Chem. Rev. 1993, 93, 763.
44. It should be mentioned that chiral α-unsubstituted-β-hydroxy carboxylic acids are also accessible by aldol-type reactions of titanium enolates, 4e,11 by reductions 12 and by enzymatic reduction 13 of β-oxo esters and by Mukaiyama-type aldolization of sultam-derived O-silyl-N,O-ketene acetals. 14 (11) (a) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. 1989, 101, 490; Angew. Chem. Int. Ed. Engl. 1989, 28, 495. (b) Cambie, R. C.; Coddington, J. M.; Milbank, J. B. J.; Pausler, M. G.; Rustenhoven, J. J.; Rutledge, P. S.; Shaw, G. L.; Sinkovich, P. I. Aust. J. Chem. 1993, 46, 583.
45. It should be mentioned that chiral α-unsubstituted-β-hydroxy carboxylic acids are also accessible by aldol-type reactions of titanium enolates, 4e,11 by reductions 12 and by enzymatic reduction 13 of β-oxo esters and by Mukaiyama-type aldolization of sultam-derived O-silyl-N,O-ketene acetals. 14 (11) (a) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. 1989, 101, 490; Angew. Chem. Int. Ed. Engl. 1989, 28, 495. (b) Cambie, R. C.; Coddington, J. M.; Milbank, J. B. J.; Pausler, M. G.; Rustenhoven, J. J.; Rutledge, P. S.; Shaw, G. L.; Sinkovich, P. I. Aust. J. Chem. 1993, 46, 583.
46. It should be mentioned that chiral α-unsubstituted-β-hydroxy carboxylic acids are also accessible by aldol-type reactions of titanium enolates, 4e,11 by reductions 12 and by enzymatic reduction 13 of β-oxo esters and by Mukaiyama-type aldolization of sultam-derived O-silyl-N,O-ketene acetals. 14 (11) (a) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. 1989, 101, 490; Angew. Chem. Int. Ed. Engl. 1989, 28, 495. (b) Cambie, R. C.; Coddington, J. M.; Milbank, J. B. J.; Pausler, M. G.; Rustenhoven, J. J.; Rutledge, P. S.; Shaw, G. L.; Sinkovich, P. I. Aust. J. Chem. 1993, 46, 583.
47. (a) Noyori, R.; Ohkumana, T.; Kitamura, M. J. Am. Chem. Soc. 1987, 109, 5856.
48. (b) Taber, D. F.; Bruce, P.; Gaul, M. D. J. Am. Chem. Soc. 1987, 109, 7488.
49. (c) Nakahata, M.; Imaida, M.; Ozaki, H.; Harada, T.; Tay, A. Bull. Chem. Soc. Jpn. 1982, 55, 2186.
50. (a) Fujisawa, T.; Itoh, T.; Sato, T. Tetrahedron Lett. 1984, 25, 5083.
51. (b) Itoh, T.; Yonekawa, Y.; Sato, T.; Fujisawa, T. Tetrahedron Lett. 1986, 27, 5405.
52. (a) Oppolzer, W.; Contelles, J. M. Helv. Chim. Acta 1986, 69, 1699.
53. (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439.
54. A sulfenyl group in the α-position of a β-oxo ester or of a β-acetoxy ester promotes stereoselective enzymatic reactions. 13,16
55. Itoh, T.; Kuroda, K.; Tomosada, M.; Takagi, Y. J. Org. Chem. 1991, 56, 797.
56. Brown, H. C.; Vara Prasad, J. V. N.; Zaidlewicz, M. J. Org. Chem. 1988, 53, 2911.
57. Devant, R.; Braun, M. Chem. Ber. 1986, 119, 2191.
58. The absolute configuration was determined on the basis of optical rotation of 3-hydroxy-5-methylhexanoic acid. 11a
59. For designing the si and re face of boron enolates 3, the rule proposed by Evans 21 was adopted as in the previous paper. 3b
60. Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol 3B, p 11.