Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3544-3547

  Alvarez Ibarra, Carlos ^a   Csákÿ, Aurelio G ^a   De La Oliva, Cristina Gómez ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ESTER DERIVATIVE; GLUTAMIC ACID DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; SYNTHESIS;

EID: 0343566437     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9918192     Document Type: Note

References (40)

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20. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
21. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
22. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
23. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
24. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
25. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
26. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
27. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
28. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
29. For some leading references on the most relevant methods for the synthesis of γ,δ-unsaturated amino acids, see the following. (i) Ene reaction of sulfonylimines: Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547. (ii) Allylation of electrophilic glycines: Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckam, W. C.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769. (iii) Allylation of nucleophilic glycines: (a) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (b) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. Ireland-Claisen reaction on allyl ester enolates: (a) Kazmaier, U.; Maier, S. Chem. Commun. 1998, 2535. (b) Miller, J. F.; Termin, A.; Koch, K. Piscopio, A. D. J. Org. Chem. 1998, 63, 3158. (c) Kazmaier, U.; Schneider, C. Synthesis 1998, 1321. Hydrogenation of conjugated dienamides: Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657. Palladium-catalyzed allylic substitutions: (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. 1997, 36, 2635. (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1468 and references cited therein.
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34. tBu in THF. See, for example: (a) Stork, G.; Leong, A. Y. W.; Touzin, A. M. J. Org. Chem. 1976, 41, 3491. (b) Hoppe, D.; Beckmann, L. Lieb. Ann. Chem. 1979, 2066. (c) Alvarez-Ibarra, C.; Csákÿ, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478.
35. tBu in THF. See, for example: (a) Stork, G.; Leong, A. Y. W.; Touzin, A. M. J. Org. Chem. 1976, 41, 3491. (b) Hoppe, D.; Beckmann, L. Lieb. Ann. Chem. 1979, 2066. (c) Alvarez-Ibarra, C.; Csákÿ, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478.
36. Alvarez Ibarra, C.; Csákÿ, A. G.; Martin Ortega, E.; de la Morena, M. J.; Quiroga, M. L. Tetrahedron Lett. 1997, 38, 4501.
37. The product of the attack of the potassium enolates of 2 to the α-carbon of 1 was not observed. This reaction course has been proposed for the addition of nitrogen nucleophiles to the α-carbon of alkynoates. See: Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
38. See, for example: Battersby, A. R.; Baker, M. G.; Broadbent, H. A.; Fookes, J. R.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1987, 2027.
39. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
40. Shipchandler, M. T. Synthesis 1979, 666.