Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis

Organic Letters

Volumn 2, Issue 19, 2000, Pages 2959-2962

  Perrard, Thierry ^a   Plaquevent, Jean Christophe ^a   Desmurs, Jean Roger ^b   Hébrault, Dominique ^b  

^a IRCOF   (France)

^b Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; PERFUME; PLANT EXTRACT;

ARTICLE; CATALYSIS; CHEMISTRY; PLANT; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLOPENTANES; PERFUME; PLANT EXTRACTS; PLANTS; STEREOISOMERISM;

EID: 0034699310     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006207e     Document Type: Article

References (34)

1. Frater, G.; Bajgrowicz, J A.; Kraft, P. Tetrahedron 1998, 54, 7633.
2. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
3. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
4. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
5. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
6. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
7. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
8. Ravid, U.; Ikan, R.; Sachs, R M. J. Agric. Food Chem. 1975, 23, 835. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Biosci. Biotech. Biochem. 1994, 58, 544 and references therein. Ishikawa, A.; Yoshihara, T.; Nakamura, K. Plant Mol. Biol. 1994, 26, 403. Zhang, Z.-P.; Krumm, T.; Baldwin, T. I. J. Chem. Ecol. 1997, 23, 2777. Koda Y. Photochemistry 1991, 30, 1435. Bodnaryk, R.; Yoshihara, T. J. Chem. Ecol. 1995, 21, 1735. Seto, H.; Kamuro, Y.; Oian, Z.; Shimizu, T. J. Pesticide Sci. 1992, 17, 61.
9. Demole, P. E. Fragrance Chemistry; Theimer, E. T., Ed.; Academic Press: Orlando, 1982.
10. Hill, R. K.; Edwards, A. G. Tetrahedron 1965, 21, 1501.
11. Ets Roure-Bertrand Fils & Justin Dupont SA, no. US3978108, filed the 12/17/71. Hasegawa K. K, no. JP224916, filed the 10/11/85. Firmenich SA, no. CH96/2, 750, filed the 11/07/96. Firmenich SA, no. WO96/00206, filed the 21/06/95. Firmenich SA, no. US5874600, filed the 07/10/97. Firmenich SA, no. WO/9800776, filed the 05/19/98. See also: Dobbs, D A.; Vanhessche, K. P. M.; Brazi, E.; Rautenstrauch, V.; Lenoir, J. Y.; Genêt, J. P.; Wiles, J.; Bergens, S. H. Angew. Chem., Int. Ed. 2000, 39, 1992.
12. Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. 2000, 39, 569.
13. The enone is commercially available from Aldrich and can also be synthesized using Rhône Poulenc Industrialisation procedure.
14. Krapcho, A. P. Synthesis 1982, 805. Krapcho, A. P. Synthesis 1982, 893.
15. Krapcho, A. P. Synthesis 1982, 805. Krapcho, A. P. Synthesis 1982, 893.
16. Corey, E. J.; Noe, M. C.; Xu, F.; Tetrahedron Lett. 1998, 39, 5347. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B.; Wainwrigh, P. G. Tetrahedron Lett. 1997, 38, 8595. O'Donnell, M. J. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher Inc.: New York, 1993; Chapter 8, p 389; Tetrahedron, Symposia in print, 1999, 55 (20).
17. Corey, E. J.; Noe, M. C.; Xu, F.; Tetrahedron Lett. 1998, 39, 5347. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B.; Wainwrigh, P. G. Tetrahedron Lett. 1997, 38, 8595. O'Donnell, M. J. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher Inc.: New York, 1993; Chapter 8, p 389; Tetrahedron, Symposia in print, 1999, 55 (20).
18. Corey, E. J.; Noe, M. C.; Xu, F.; Tetrahedron Lett. 1998, 39, 5347. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B.; Wainwrigh, P. G. Tetrahedron Lett. 1997, 38, 8595. O'Donnell, M. J. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher Inc.: New York, 1993; Chapter 8, p 389; Tetrahedron, Symposia in print, 1999, 55 (20).
19. Corey, E. J.; Noe, M. C.; Xu, F.; Tetrahedron Lett. 1998, 39, 5347. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B.; Wainwrigh, P. G. Tetrahedron Lett. 1997, 38, 8595. O'Donnell, M. J. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher Inc.: New York, 1993; Chapter 8, p 389; Tetrahedron, Symposia in print, 1999, 55 (20).
20. Corey, E. J.; Noe, M. C.; Xu, F.; Tetrahedron Lett. 1998, 39, 5347. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B.; Wainwrigh, P. G. Tetrahedron Lett. 1997, 38, 8595. O'Donnell, M. J. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher Inc.: New York, 1993; Chapter 8, p 389; Tetrahedron, Symposia in print, 1999, 55 (20).
21. 3). Anal. Calcd: C, 76.28; H, 6.40; N, 5.08. Found: C, 75.98; H, 6.44: N, 5.36.
22. 3). Anal. Calcd: C, 76.28; H, 6.40; N, 5.08. Found: C, 75.98; H, 6.44: N, 5.36.
23. 3). Anal. Calcd: C, 76.28; H, 6.40; N, 5.08. Found: C, 75.98; H, 6.44: N, 5.36.
24. Potassium carbonate can be replaced by either rubidium and cesium carbonate or by Schwesinger's bases as well as potassium tert-butoxide; on the other hand, lithium or sodium carbonate and potassium hydrogen carbonate failed to promote the reaction.
25. 5: C, 63.36; H, 8.51. Found: C, 63.58; H, 8.77.
26. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233. Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473. Mirza-Aghayan, M.; Etemad-Moghadam, G.; Zaparucha, A.; Berlan, J.; Loupy, A.; Koenig, M. Tetrahedron: Asymmetry 1995, 6, 2643.
27. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233. Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473. Mirza-Aghayan, M.; Etemad-Moghadam, G.; Zaparucha, A.; Berlan, J.; Loupy, A.; Koenig, M. Tetrahedron: Asymmetry 1995, 6, 2643.
28. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233. Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473. Mirza-Aghayan, M.; Etemad-Moghadam, G.; Zaparucha, A.; Berlan, J.; Loupy, A.; Koenig, M. Tetrahedron: Asymmetry 1995, 6, 2643.
29. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233. Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473. Mirza-Aghayan, M.; Etemad-Moghadam, G.; Zaparucha, A.; Berlan, J.; Loupy, A.; Koenig, M. Tetrahedron: Asymmetry 1995, 6, 2643.
30. Colonna, S.; Annunziata, R. Afinidad 1980, 38, 501. Loupy, A.; Bram, G.; Sansoulet, J. New. J. Chem. 1992, 16, 233.
31. Colonna, S.; Annunziata, R. Afinidad 1980, 38, 501. Loupy, A.; Bram, G.; Sansoulet, J. New. J. Chem. 1992, 16, 233.
32. 3: C, 68.99; H, 9.80. Found: C, 68.64; H, 9.98.
33. 3: C, 68.99; H, 9.80. Found: C, 68.64; H, 9.98.
34. For a recent related example of highly enantioselective Michael reaction, see: Zhang, F.-Y.; Corey, E. J. Org. Lett 2000, 2, 1097.