Asymmetric PTC Alkylation of Glycine Imines: Variation of the Imine Ester Moiety

Synlett

Volumn , Issue 2, 2004, Pages 326-328

  Lygo, Barry ^a   Allbutt, Bryan ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Amino acids; Asymmetric alkylation; Phase transfer catalysis; Quaternary ammonium salts

Indexed keywords

AMINO ACID; AMMONIUM DERIVATIVE; ASPARTIC ACID; BENZHYDRYL DERIVATIVE; BENZYL DERIVATIVE; CINCHONIDINE; ESTER; GLYCINE; IMINE; NAPHTHALENE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; HYDROLYSIS; PHASE TRANSITION;

EID: 1242273664     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43368     Document Type: Article

References (33)

1. For recent reviews covering phase-transfer alkylation of glycine imines see: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013. (b) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
2. For recent reviews covering phase-transfer alkylation of glycine imines see: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013. (b) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
3. (a) Lygo, B.; Allbutt, B.; James, S. R. Tetrahedron Lett. 2003, 44, 5629.
4. (b) Lygo, B.; Andrews, B. I.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 2002, 43, 8015.
5. (c) Lygo, B.; Humphreys, L. D. Tetrahedron Lett. 2002, 43, 6677.
6. (d) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 6447.
7. (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403.
8. (f) Lygo, B.; Crosby, J.; Lowdon, T. R.; Wainwright, P. G. Tetrahedron 2001, 57, 2391.
9. (g) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385.
10. (h) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595.
11. 1a see ref. 1 and: (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579; amides, (b) Mazon, P.; Chinchilla, R.; Najera, C.; Guillena, G.; Kreiter, R.; Gebbink, R. J. M. K.; van Koten, G. Tetrahedron: Asymmetry 2002, 13, 2181; iso-propyl ester, (c) Vyskocil, S.; Meca, L.; Tislerova, I.; Cisarova, I.; Polasek, M.; Harutyunyan, S. R.; Belokon, Y. N.; Stead, R. M. J.; Farrugia, L.; Lockhart, S. C.; Mitchell, W. L.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4633; Ni salt of PBP imine.
12. 1a see ref. 1 and: (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579; amides, (b) Mazon, P.; Chinchilla, R.; Najera, C.; Guillena, G.; Kreiter, R.; Gebbink, R. J. M. K.; van Koten, G. Tetrahedron: Asymmetry 2002, 13, 2181; iso-propyl ester, (c) Vyskocil, S.; Meca, L.; Tislerova, I.; Cisarova, I.; Polasek, M.; Harutyunyan, S. R.; Belokon, Y. N.; Stead, R. M. J.; Farrugia, L.; Lockhart, S. C.; Mitchell, W. L.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4633; Ni salt of PBP imine.
13. 1a see ref. 1 and: (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579; amides, (b) Mazon, P.; Chinchilla, R.; Najera, C.; Guillena, G.; Kreiter, R.; Gebbink, R. J. M. K.; van Koten, G. Tetrahedron: Asymmetry 2002, 13, 2181; iso-propyl ester, (c) Vyskocil, S.; Meca, L.; Tislerova, I.; Cisarova, I.; Polasek, M.; Harutyunyan, S. R.; Belokon, Y. N.; Stead, R. M. J.; Farrugia, L.; Lockhart, S. C.; Mitchell, W. L.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4633; Ni salt of PBP imine.
14. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
15. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
16. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
17. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
18. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
19. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
20. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
21. 2, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (c) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Lee, J. H.; Park, B. S.; Kim, M. J.; Jew, S. S. Tetrahedron Lett. 2003, 44, 3497. (d) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671. (e) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (f) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515. (g) Chen, G.; Deng, Y.; Gong, L.; Mi, A. ; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. (h) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
22. 4a and: (a) Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703. (b) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (c) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499. (d) Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
23. 4a and: (a) Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703. (b) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (c) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499. (d) Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
24. 4a and: (a) Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703. (b) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (c) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499. (d) Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
25. 4a and: (a) Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703. (b) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (c) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499. (d) Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
26. 4a and: (a) Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703. (b) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (c) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499. (d) Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
27. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
28. For examples that illustrate of the utility of this see: (a) Mitchell, S. A.; Pratt, M. R.; Hruby, V. J.; Polt, R. J. Org. Chem. 2001, 66, 2327. (b) Tilley, J. W.; Sarabu, R.; Wagner, R.; Mulkerins, K. J. Org. Chem. 1990, 55, 906. (c) Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki. C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194.
29. For examples that illustrate of the utility of this see: (a) Mitchell, S. A.; Pratt, M. R.; Hruby, V. J.; Polt, R. J. Org. Chem. 2001, 66, 2327. (b) Tilley, J. W.; Sarabu, R.; Wagner, R.; Mulkerins, K. J. Org. Chem. 1990, 55, 906. (c) Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki. C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194.
30. For examples that illustrate of the utility of this see: (a) Mitchell, S. A.; Pratt, M. R.; Hruby, V. J.; Polt, R. J. Org. Chem. 2001, 66, 2327. (b) Tilley, J. W.; Sarabu, R.; Wagner, R.; Mulkerins, K. J. Org. Chem. 1990, 55, 906. (c) Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki. C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194.
31. O'Donnell, M. J.; Sennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
32. 3)
33. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.