Convenient enzymatic resolution of alcohols using highly reactive, nonharmful acyl donors, 1-ethoxyvinyl esters

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 83-88

  Kita, Yasuyuki ^a   Takebe, Yasushi ^a   Murata, Kenji ^a   Naka, Tadaatsu ^a   Akai, Shuji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ESTER DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033972206     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910785     Document Type: Article

References (56)

1. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
2. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
3. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
4. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
5. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
6. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
7. For recent reviews, see: (a) Faber, K.; Riva, S. Synthesis 1992, 895-910. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; pp 41-130. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 668-677. (d) Theil, F. Chem. Rev. 1995, 95, 2203-2227. (e) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. (f) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer- Verlag: Berlin, 1997. (g) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608-1633.
8. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072-7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
9. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
10. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
11. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
12. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
13. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
14. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
15. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
16. Trifluoroethyl esters and chloroethyl esters: (a) Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072- 7076. Cyanomethyl esters: (b) West, J. B.; Scholten, J.; Stolowich, N. J.; Hogg, J. L.; Scott, A. I.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 3709-3710. Oxime esters: (c) Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535. (d) Gotor, V.; Pulido, R. J. Chem. Soc., Perkin Trans. 1 1991, 491-492. (e) Mischitz, M.; Pöschl, U.; Faber, K. Biotechnol. Lett. 1991, 13, 653-656. (f) Pulido, R.; Ortiz, F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2891-2898. (g) Gotor, V.; Moris, F. Synthesis 1992, 626-628. Acid anhydrides: (h) Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534. (i) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817-3818.
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25. We have disclosed various types of very mild and convenient reactions utilizing the ketene acetal reagents I. Thus, the reactions with nucleophiles (Nu-H) proceed in inert solvents at room-to-moderate temperature to give the products II accompanied by formation of volatile esters III as the only coproducts. Simple concentration of the reaction mixture gives pure II in high yields. For reviews, see: Kita, Y.; Tamura, O.; Tamura, Y. J. Synth. Org. Chem. Jpn. 1986, 44, 1118-1133. Kita, Y.; Shibata, N. Synlett 1996, 289-296.
26. We have disclosed various types of very mild and convenient reactions utilizing the ketene acetal reagents I. Thus, the reactions with nucleophiles (Nu-H) proceed in inert solvents at room-to-moderate temperature to give the products II accompanied by formation of volatile esters III as the only coproducts. Simple concentration of the reaction mixture gives pure II in high yields. For reviews, see: Kita, Y.; Tamura, O.; Tamura, Y. J. Synth. Org. Chem. Jpn. 1986, 44, 1118- 1133. Kita, Y.; Shibata, N. Synlett 1996, 289-296.
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36. For examples, see: Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. Nair, M. S.; Anilkumar, A. T. Tetrahedron: Asymmetry 1996, 7, 511-514. Chênevert, R.; Goupil, D.; Rose, Y. S.; Bédard, E. Tetrahedron: Asymmetry 1998, 9, 4285-4288.
37. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
38. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
39. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
40. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
41. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
42. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
43. For examples, see: Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091-2994. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625-628; J. Org. Chem. 1996, 61, 8610-8816. Nakamura, K.; Takenaka, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 4429-4439. For the use of vinyl benzoate and vinyl phenylacetate, see: Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849-2854.
44. For an example, see: Akai S.; Naka T.; Takebe Y.; Kita Y. Tetrahedron Lett. 1997, 38, 4243-4246.
45. 4. See: Swern, D.; Jordan, E. F., Jr. Organic Syntheses; Wiley: New York, 1963, Collect. Vol. 4, pp 977-980.
46. 4. See: Swern, D.; Jordan, E. F., Jr. Organic Syntheses; Wiley: New York, 1963, Collect. Vol. 4, pp 977-980.
47. 4. See: Swern, D.; Jordan, E. F., Jr. Organic Syntheses; Wiley: New York, 1963, Collect. Vol. 4, pp 977-980.
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