A highly efficient asymmetric synthesis of optically active α,γ-substituted γ-butyrolactones using a chiral auxiliary derived from isosorbide

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2229-2232

  Xu, Ming Hua ^a   Wang, Wei ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE; ISOSORBIDE; KETONE; METHACRYLIC ACID DERIVATIVE; PROTON;

ARTICLE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ISOSORBIDE; KETONES; METHACRYLATES; PROTONS; STEREOISOMERISM;

EID: 0034720960     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005978f     Document Type: Article

References (35)

1. (a) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. J. Org. Chem. 1998, 63, 2385-2388.
2. (b) Rodriguez, C. M.; Martin, T.; Martin, V. S. J. Org. Chem. 1996, 61, 8448-8452.
3. (a) Koch, S. S. C.; Chamberline, A. R. J. Org. Chem. 1993, 58, 2725-2737.
4. (b) Grimm, E. L.; Reissig, H. U. J. Org. Chem. 1985, 50, 242-244.
5. For transformation of chiral natural products, see: (a) Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett.1992, 33, 4931-4932.
6. (b) Yoda, H.; Shirakawa, K.; Takabe, K. Chem. Lett. 1991, 489-490.
7. (c) Yoda, H.; Shirakawa, K.; Takabe, K. Tetrahedron Lett.1991, 32, 3401-3404.
8. For dehydration of chiral γ-hydroxyl acid, see: (d) Ramachandran, P. V.; Krzeminski, M. P.; Venkat, M.; Reddy, R.; Brown, H. C. Tetrahedron: Asymmetry, 1999, 10, 11-15.
9. (e) Boly, V.; Vigneron, J. P. Tetrahedron Lett. 1980, 21, 1735.
10. (f) Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369.
11. For induction of chiral auxiliaries, see: (g) Yammamoto, Y.; Sakamoto, A.; Nishioka, T.; Oda, J.; Fukazawa, Y. J. Org. Chem. 1991, 56, 1112-1119.
12. (h) Nair, V.; Prabhakaran, J. J. Chem. Soc., Perkin Trans. 1 1996, 593-594.
13. (i) Nair, V.; Prabhakaran, J.; George, T. G. Tetrahedron 1997, 44, 15061-15068.
14. (j) Taniguch, N.; Uemura, M. Tetrahedron Lett. 1997, 38, 7199-7202.
15. (k) Merlic, C. A.; Walsh, J. C. Tetrahedron Lett. 1998, 39, 2083-2086.
16. For catalysis mediated by chiral metal complexes, see: (l) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509-5512.
17. (m) Doyle, M. P.; Protopopova, M. N.; Zhou, Q.-L.; Bode, J. W. J. Org. Chem. 1995, 60, 6654-6655.
18. (n) Yu, W. Y.; Bensimon, C.; Alper, H. Chem. Eur. J. 1997, 3, 417-423.
19. (o) Cao, P.; Zhang, X. J. Am. Chem. Soc. 1999, 121, 7708-7709.
20. For ligand-controlled asymmetric synthesis, see: (p) Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501-4504.
21. Fukuzawa, S.; Seki, K.; Tatsuzawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482-1483.
22. During the preparation of this manuscript, a method was reported for the synthesis of cis-α,γ-dialkyl γ-lactones using chiral sec-dialkyl bishomopropargylic alcohols as the reactant; see: Diaz, D.; Martin, V. S.; Org. Lett. 2000, 2, 335-337.
23. Xu, M.-H.; Lin, G.-Q.; Xia, L.-J.; Chin. J. Chem. 1998, 16, 561-564.
24. Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1988, 1669-1675.
25. For a review of asymmetric protonation of enolates and enols, see: (a) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566-2587.
26. For examples of asymmetric protonation of samarium enolates, see: (b) Takeuchi, S.; Miyoshi, N.; Ohgo, Y. Chem. Lett. 1992, 551-554.
27. (c) Takeuchi, S.; Ohira, A.; Miyoshi, N.; Mashio, H.; Ohgo, Y. Tetrahedron: Asymmetry 1994, 5, 1763-1780.
28. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805-2808.
29. (e) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yomaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709-2712.
30. (f) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691-8694.
31. Xu, M.-H. Ph. D. dissertation, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China, 1999. The detailed and further investigations of the asymmetric protonations will be published elsewhere.
32. Wang, J.-Q.; Xu, M.-H.; Zhong, M.; Lin, G.-Q. Chin. Chem. Lett. 1998, 9, 325-328.
33. In an effort to maximize the results, other chiral auxiliaries were also surveyed. With N-isopropylephedrine (2) as chiral auxiliary, chiral γ-butyrolactone 1 was obtained in only 30% ee. However, 2 is a good chiral auxiliary in the synthesis of chiral 4-substituted- and cis-3,4-disubstituted-γ-butyrolactones; see: note (12) of ref 4.
34. Since (-)-sultam (4) is commercially available and not expensive, we still use it as the chiral proton source instead of (±)-sultam.
35. -3.