Regioselective carbomethoxylation of chiral epoxides: A new route to enantiomerically pure β-hydroxy esters

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2164-2165

  Hinterding, Klaus ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; CARBOXYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033515487     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982336l     Document Type: Article

References (20)

1. (a) Drent, E.; Kragtwijk, E. Eur. Pat. Appl. 577206, 30 Mar. 1994; Chem Abstr. 1994, 120, 191517c.
2. (a) Drent, E.; Kragtwijk, E. Eur. Pat. Appl. 577206, 30 Mar. 1994; Chem Abstr. 1994, 120, 191517c.
3. (b) For earlier work, see: Eisenmann, J. L.; Yamartino, R. L.; Howard, J. F. J. Org. Chem. 1961, 26, 2102.
4. (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F. ; Jacobsen, E. N. Science 1997, 277, 936.
5. (b) Brandes, B. D.; Jacobsen, E. N. Tetrahedron: Asymmetry 1997, 8, 3927.
6. (c) Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776.
7. (a) Yokokawa, C.; Watanabe, Y.; Takegami, Y. Bull. Chem. Soc. Jpn. 1964, 37, 677.
8. (b) Takegami, Y.; Yokokawa, C.; Watanabe, Y. Bull. Chem. Soc. Jpn. 1964, 37, 935.
9. (c) Roos, L.; Goetz, R.W.; Orchin, M. J. Org. Chem. 1965, 30, 3203.
10. (c) Rosenthal, A.; Kan, G. Tetrahedron Lett. 1967, 477.
11. 1H NMR.
12. Carboalkoxylations of olefins generally require much harsher conditions than those employed here. See, for example: Takeuchi, R.; Ishii, N.; Sugiura, M.; Sato, N. J. Org. Chem. 1992, 57, 4189. For reviews see: (a) Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 101-223.
13. Carboalkoxylations of olefins generally require much harsher conditions than those employed here. See, for example: Takeuchi, R.; Ishii, N.; Sugiura, M.; Sato, N. J. Org. Chem. 1992, 57, 4189. For reviews see: (a) Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 101-223.
14. (b) Bates, R. W. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995, Vol. 12, pp 349-386.
15. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937.
16. The reaction was carried out on a 200 mmol scale for (S)-propylene oxide 3a (65 °C, 600 psi, 24 h) using only MeOH (200 mL) as solvent. (S)-Methyl-3-hydroxybutyrate 6a was obtained in 83% yield by distillation (regioselectivity: 1/b > 60/1; no racemization detectable).
17. 2OBn 7g: 90% yield
18. Benzyl amides can also be prepared by an analogous procedure. See: Tsuji, Y.; Kobayashi, M.; Okuda, F.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1989, 1253.
19. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Chapter 2, pp 28-55. For a leading reference on asymmetric catalytic aldol approaches to simple β-hydroxy carbonyl compounds, see: Carreira, E. M.; Singer, R. A.; Lee, W. S. J. Am. Chem. Soc. 1994, 116, 8837.
20. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Chapter 2, pp 28-55. For a leading reference on asymmetric catalytic aldol approaches to simple β-hydroxy carbonyl compounds, see: Carreira, E. M.; Singer, R. A.; Lee, W. S. J. Am. Chem. Soc. 1994, 116, 8837.