Pseudomonas cepacia lipase mediated amidation of benzyl esters

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7913-7916

  Adamczyk, Maciej ^a   Grote, Jonathan ^a  

^a ABBOTT DIAGNOSTICS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS;

BURKHOLDERIA; BURKHOLDERIA CEPACIA; PSEUDOMONAS;

EID: 0030605101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01792-3     Document Type: Article

References (28)

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10. 9. For leading references: β-keto esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 23, 6935-6940; β-hydroxy esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 2199-210; β-aryl esters: Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans. 1 1993, 2453-6; α,β-unsaturated esters: Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett 1994, 529-30; α-halo esters: Quiros, M.; Sanchez, V. M.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 1105-12; diesters: Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-32.
11. 9. For leading references: β-keto esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 23, 6935-6940; β-hydroxy esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 2199-210; β-aryl esters: Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans. 1 1993, 2453-6; α,β-unsaturated esters: Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett 1994, 529-30; α-halo esters: Quiros, M.; Sanchez, V. M.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 1105-12; diesters: Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-32.
12. 9. For leading references: β-keto esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 23, 6935-6940; β-hydroxy esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 2199-210; β-aryl esters: Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans. 1 1993, 2453-6; α,β-unsaturated esters: Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett 1994, 529-30; α-halo esters: Quiros, M.; Sanchez, V. M.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 1105-12; diesters: Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-32.
13. 9. For leading references: β-keto esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 23, 6935-6940; β-hydroxy esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 2199-210; β-aryl esters: Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans. 1 1993, 2453-6; α,β-unsaturated esters: Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett 1994, 529-30; α-halo esters: Quiros, M.; Sanchez, V. M.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 1105-12; diesters: Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-32.
14. 9. For leading references: β-keto esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 23, 6935-6940; β-hydroxy esters: Garcia, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 2199-210; β-aryl esters: Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans. 1 1993, 2453-6; α,β-unsaturated esters: Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett 1994, 529-30; α-halo esters: Quiros, M.; Sanchez, V. M.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1993, 4, 1105-12; diesters: Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-32.
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25. 18. The solvents used were anhydrous grade (Aldrich) and used as received.
26. 19. Zaks, A.; Klibanov, A.M. J. Am. Chem. Soc. 1986, 108, 2767-2768, footnote 5.
27. 20. Faber, S.; Riva, S. Synthesis 1992, 895-910.
28. 13C NMR (CDCl3) δ 167.4, 165.9, 160.8, 138.4, 136.1, 132.0, 128.8, 128.7, 128.6, 128.3, 128.2, 126.7, 124.1, 114.3, 67.2, 66.6, 40.4, 35.5; ESMS (M + H)+ at 390. Crystallization from ethyl acetate / hexane provided fine white needles with mp 107-108°.