Sequential acyl halide-aldehyde cyclocondensation and enzymatic resolution as a route to enantiomerically enriched β-lactones

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1227-1230

  Nelson, Scott G ^a   Spencer, Keith L ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

ACETATES; ALDEHYDES; CATALYSIS; LACTONES; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0034712238     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9913412     Document Type: Article

References (40)

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21. For reviews of enzyme-mediated asymmetric reactions, see: (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Weinheim, Germany, 1992. (b) Halgas, J. Biocatalysis in Organic Synthesis; Elsevier: New York, 1992. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140. (d) Wong, C.-H., Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995. (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahdron 1996, 52, 3796-3826. (g) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997. (h) Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1-20.
22. For reviews of enzyme-mediated asymmetric reactions, see: (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Weinheim, Germany, 1992. (b) Halgas, J. Biocatalysis in Organic Synthesis; Elsevier: New York, 1992. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140. (d) Wong, C.-H., Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995. (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahdron 1996, 52, 3796-3826. (g) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997. (h) Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1-20.
23. For reviews of enzyme-mediated asymmetric reactions, see: (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Weinheim, Germany, 1992. (b) Halgas, J. Biocatalysis in Organic Synthesis; Elsevier: New York, 1992. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140. (d) Wong, C.-H., Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995. (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahdron 1996, 52, 3796-3826. (g) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997. (h) Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1-20.
24. For reviews of enzyme-mediated asymmetric reactions, see: (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Weinheim, Germany, 1992. (b) Halgas, J. Biocatalysis in Organic Synthesis; Elsevier: New York, 1992. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140. (d) Wong, C.-H., Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995. (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahdron 1996, 52, 3796-3826. (g) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997. (h) Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1-20.
25. For reviews of enzyme-mediated asymmetric reactions, see: (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Weinheim, Germany, 1992. (b) Halgas, J. Biocatalysis in Organic Synthesis; Elsevier: New York, 1992. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140. (d) Wong, C.-H., Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995. (f) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahdron 1996, 52, 3796-3826. (g) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997. (h) Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1-20.
26. For some examples of asymmetric enzyme-mediated lactone ring-opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
27. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
28. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
29. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,-N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
30. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
31. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
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33. For some examples of asymmetric enzyme-mediated lactone ring- opening, see: (a) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.; Guerzoni, M. E. Tetrahedron: Asymmetry 1992, 3, 107-114. (b) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511-6520. (c) Fellous, R.; Lizzanicuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. (d) Ha, H.-J.; Yi, D.-G.; Yoon, K,- N.; Song, C.-W. Bull. Kor. Chem. Soc. 1996, 17, 544-547. (e) Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 4519-4522. (f) Onakunle, O. A.; Knowles, C. J.; Bunch, A. W. Enzyme Microb. Technol. 1997, 21, 245-251. (g) Enzelberger, M. M.; Bornscheuer, U. T.; Gatfield, I.; Schmid, R. D. J. Biotechnol. 1997, 56, 129-133. (h) Ha, H.-J.; Yoon, K.-N.; Lee, S.-Y.; Park, Y.-S.; Lim, M.-S.; Yim, Y.-G. J. Org. Chem. 1998, 63, 8062-8066.
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