Enantiomeric Enrichment of Allenedicarboxylates by a Chiral Organoeuropium Reagent

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3862-3866

  Naruse, Yuji ^a   Watanabe, Hidefumi ^a   Ishiyama, Yasuhiro ^a   Yoshida, Tomoe ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000631819     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961870v     Document Type: Article

References (40)

1. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
2. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
3. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
4. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
5. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
6. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
7. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
8. Duhamel, L.; Duhamel, P.; Launay, J. C.; Plaquevant, J. C. Bull. Soc. Chim. Fr. 1984, II-421. "Enantiomeric enrichment" described here is a thermodynamic process. The term "deracemization" includes kinetic processes as well as thermodynamie ones. See also ref 6, note 5. There are many papers which report kinetic asymmetric protonation. For a review: Fehr, C. Chimia 1991, 45, 253. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. Some recent works: Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805; and references cited therein. For the synthetic equivalent of this transformation: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
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15. The following papers have recently appeared in the literature: Organometallic reagents: (a) Schlosser M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. (b) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (c) Park, Y. S.; Mark, L. B.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. (d) Hoffmann, R. W.; Klute, W. Chem. Eur. J. 1996, 2, 694. (e) Basu, A.; Gallapher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
16. The following papers have recently appeared in the literature: Organometallic reagents: (a) Schlosser M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. (b) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (c) Park, Y. S.; Mark, L. B.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. (d) Hoffmann, R. W.; Klute, W. Chem. Eur. J. 1996, 2, 694. (e) Basu, A.; Gallapher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
17. The following papers have recently appeared in the literature: Organometallic reagents: (a) Schlosser M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. (b) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (c) Park, Y. S.; Mark, L. B.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. (d) Hoffmann, R. W.; Klute, W. Chem. Eur. J. 1996, 2, 694. (e) Basu, A.; Gallapher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
18. The following papers have recently appeared in the literature: Organometallic reagents: (a) Schlosser M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. (b) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (c) Park, Y. S.; Mark, L. B.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. (d) Hoffmann, R. W.; Klute, W. Chem. Eur. J. 1996, 2, 694. (e) Basu, A.; Gallapher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
19. The following papers have recently appeared in the literature: Organometallic reagents: (a) Schlosser M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. (b) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (c) Park, Y. S.; Mark, L. B.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. (d) Hoffmann, R. W.; Klute, W. Chem. Eur. J. 1996, 2, 694. (e) Basu, A.; Gallapher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
20. Enamines: (f) Kitamura, M.; Tsukamoto, M.; Takaya, H.; Noyori, R. Bull. Chem. Soc. Jpn. 1996, 69, 1695.
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22. See also: (h) Krois D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085. Meyers reported chiral oxazoline-assisted deracemization of biaryl compounds: (i) Nelson T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259; (j) Nelson T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655; (k) Meyers A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5849.
23. See also: (h) Krois D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085. Meyers reported chiral oxazoline-assisted deracemization of biaryl compounds: (i) Nelson T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259; (j) Nelson T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655; (k) Meyers A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5849.
24. See also: (h) Krois D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085. Meyers reported chiral oxazoline-assisted deracemization of biaryl compounds: (i) Nelson T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259; (j) Nelson T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655; (k) Meyers A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5849.
25. See also: (h) Krois D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085. Meyers reported chiral oxazoline-assisted deracemization of biaryl compounds: (i) Nelson T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259; (j) Nelson T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655; (k) Meyers A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5849.
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27. Naruse, Y.; Watanabe, H.; Inagaki, S. Tetrahedron: Asymmetry 1992, 3, 603.
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30. Trost reported isomerization of acetylenecarboxylates and allenecarboxylates to conjugated α,γ-dienoates using triphenylphosphine. Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933.
31. Naruse, Y.; Sakou, S. Unpublished results.
32. Naruse, Y. Unpublished results.
33. Ikeda, I.; Honda, K.; Osawa, E.; Shiro, M.; Aso, M.; Kanematsu, K. J. Org. Chem. 1996, 61, 2031.
34. 3 is an effective chiral Lewis acid for the hetero DielsAlder reaction. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1985, 105, 3716.
35. Preparation of dimethyl 2,3-pentadienedioate: Bryson T. A.; Dolak, T. M. In Organic Syntheses; John Wiley and Sons, Inc.: New York, 1988; Collect. Vol. VI, pp 505-507.
36. Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690, note 13.
37. Runge, W. In The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley and Sons, Inc.: New York, 1980; Part 1, pp 232-235. Runge, W. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982; Vol. 3, pp 580-594.
38. Runge, W. In The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley and Sons, Inc.: New York, 1980; Part 1, pp 232-235. Runge, W. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982; Vol. 3, pp 580-594.
39. Preparation of allenecarboxylates: Lang, R. W.; Hansen, H.-J. In Organic Syntheses; John Wiley and Sons, Inc.: New York, 1990; Collect Vol. VII, pp 232-235.
40. From Aldrich Chemical Co.