Homocarbonates as substrates for the enantioselective enzymatic protection of amines

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 712-713

  Orsat, Bernard ^a   Alper, Phil B ^a   Moree, Wilna ^a   Mak, Ching Pong ^b   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Sandoz Pharma Ltd   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000127204     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9533048     Document Type: Article

References (18)

1. For a comprehensive documentation of enzymatic acylations, see: Klibanov, A.M. Acc. Chem. Res. 1990, 23, 114. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; p 72. Fang, J.-M.; Wong, C.-H. Synlett 1994, 6, 393.
2. For a comprehensive documentation of enzymatic acylations, see: Klibanov, A.M. Acc. Chem. Res. 1990, 23, 114. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; p 72. Fang, J.-M.; Wong, C.-H. Synlett 1994, 6, 393.
3. For a comprehensive documentation of enzymatic acylations, see: Klibanov, A.M. Acc. Chem. Res. 1990, 23, 114. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; p 72. Fang, J.-M.; Wong, C.-H. Synlett 1994, 6, 393.
4. Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421. Degueil-Castaing, M.; Jeso, B. D.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953. Wang, Y. F.; Lalonde, J. J.; Homongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Laumen, K.; Brietgoff, D.; Schneider, M.-P. J. Chem. Soc., Chem. Commun. 1988, 1459.
5. Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421. Degueil-Castaing, M.; Jeso, B. D.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953. Wang, Y. F.; Lalonde, J. J.; Homongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Laumen, K.; Brietgoff, D.; Schneider, M.-P. J. Chem. Soc., Chem. Commun. 1988, 1459.
6. Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421. Degueil-Castaing, M.; Jeso, B. D.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953. Wang, Y. F.; Lalonde, J. J.; Homongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Laumen, K.; Brietgoff, D.; Schneider, M.-P. J. Chem. Soc., Chem. Commun. 1988, 1459.
7. Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421. Degueil-Castaing, M.; Jeso, B. D.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953. Wang, Y. F.; Lalonde, J. J.; Homongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Laumen, K.; Brietgoff, D.; Schneider, M.-P. J. Chem. Soc., Chem. Commun. 1988, 1459.
8. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6411. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725. For other enzymatic resolutions of amines via reactions with esters to form amides, see: Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1992, 2885. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gasset, A. J. Chem. Soc., Chem. Commun. 1993, 2453.
9. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6411. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725. For other enzymatic resolutions of amines via reactions with esters to form amides, see: Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1992, 2885. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gasset, A. J. Chem. Soc., Chem. Commun. 1993, 2453.
10. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6411. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725. For other enzymatic resolutions of amines via reactions with esters to form amides, see: Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1992, 2885. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gasset, A. J. Chem. Soc., Chem. Commun. 1993, 2453.
11. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6411. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725. For other enzymatic resolutions of amines via reactions with esters to form amides, see: Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1992, 2885. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gasset, A. J. Chem. Soc., Chem. Commun. 1993, 2453.
12. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6411. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725. For other enzymatic resolutions of amines via reactions with esters to form amides, see: Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1992, 2885. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gasset, A. J. Chem. Soc., Chem. Commun. 1993, 2453.
13. Dimethyl , diethyl, and diallyl carbonates were purchased from Aldrich Chemical Co. Dibenzyl carbonate was from Lancaster Synthesis Inc.
14. Subtilisin BPN' (Nagarse, type XXVII. 8.3 units/mg, P4789) and lipase from Candida cylindracea (CCL, type VII, 860 units/mg. L1754, EC 3.1.1.3) were purchased from Sigma.
15. An identical reaction without enzyme did not give any detectable product over the same period.
16. Sennyey, G.; Barcelo, G.; Senet, J.-P. Tetrahedron Lett. 1987, 28, 5809.
17. Kunz, H.; Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1984, 23, 436.
18. Faber, K.; Hönig, H.; Seufer-Wasserthal, P. Tetrahedron Lett. 1988, 29, 1903.