A biocatalytic route to enantioenriched, sulfanyl aldol products

Tetrahedron

Volumn 60, Issue 35, 2004, Pages 7607-7619

  Baker Glenn, C ^a   Ancliff, R ^b   Gouverneur, V ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Aldol additon; Catalytic antibodies; Sulfur

Indexed keywords

ACETONE; AMIDE; ESTER DERIVATIVE; SELENIUM; SULFUR DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; KINETICS; PRIORITY JOURNAL;

EID: 3843068983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.033     Document Type: Article

References (30)

1. Fox D.J., House D., Warren S. Angew. Chem., Int. Ed. 41:2002;2462
2. Aggarwal V.K., Coldham I., McIntyre S.M., Sansbury F.H., Villa M.J., Warren S. Tetrahedron Lett. 29:1988;4885
3. Eames J., Jones R.V.H., Warren S. Tetrahedron Lett. 37:1996;4823
4. Eames J., Delasheras M.A., Warren S. Tetrahedron Lett. 37:1996;4077
5. Eames J., Warren S. Tetrahedron Lett. 37:1996;3525
6. Solladie G., Salom-Roig X.J., Hanquet G. Tetrahedron Lett. 41:2000;551
7. Carlisle J., Fox D.J., Warren S. Chem. Commun. 21:2003;2696. and references therein
8. Maggiotti V., Resmini M., Gouverneur V. Angew. Chem., Int. Ed. 41:2002;1012
9. For other references covering the generation and reactivity of aldolase antibodies, see for example: Wagner J., Lerner R.A., Barbas C.F. III. Science. 270:1995;1797
10. Björnestedt R., Zhong G., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 118:1996;11720
11. Zhong G., Hoffmann T., Lerner R.A., Danishefsky S., Barbas C.F. III. J. Am. Chem. Soc. 119:1997;8131
12. Barbas C.F. III, Heine A., Zhong G., Hoffmann T., Gramatikova S., Björnestedt R., List B., Anderson J., Stura E.A., Wilson I.A., Lerner R.A. Science. 278:1997;2085
13. Hoffmann T., Zhong G., List B., Shabat D., Anderson J., Gramatikova S., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 120:1998;2768
14. Zhong G., Shabat D., List B., Anderson J., Sinha S.C., Lerner R.A., Barbas C.F. III. Angew. Chem., Int. Ed. 37:1998;2481
15. List B., Shabat D., Zhong G., Turner J.M., Li A., Bui T., Anderson J., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 121:1999;7283
16. Zhong G., Lerner R.A., Barbas C.F. III. Angew. Chem., Int. Ed. 38:1999;3738
17. Hoffmann T., Zhong G., List B., Shabat D., Anderson J., Gramatikova S., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 120:1998;2768
18. Lerner R.A., Barbas C.F. III. Acta Chem. Scand. 36:1996;2575
19. Maggiotti V., Bahmanyar S., Reiter M., Resmini M., Houk K.N., Gouverneur V. Tetrahedron. 60:2004;619
20. See Section 4 for detailed procedures
21. Aggarwal V.K., Eames J., Villa M.-J., Mc Intyre S., Sansbury F.H., Warren S. Perkin 1. 4:2000;533
22. Ishibashi H., Kameoka C., Iriyama H., Kodama K., Sato T., Ikeda M. J. Org. Chem. 60:1995;1276
23. Bauda R., Petrzilka M. Helv. Chim. Acta. 62:1979;1406
24. All attempts to prepare chemically the product of self-aldolisation of phenylthioacetaldehyde proved to be unsuccessful
25. Hayakawa R., Shimizu M., Fujisawa T. Tetrahedron Lett. 37:1996;7533
26. Sibi M.P., Marvin M., Sharma R. J. Org. Chem. 60:1995;5016
27. Maggiotti V., Wong J.-B., Razet R., Cowley A.R., Gouverneur V. Tetrahedron: Asymmetry. 13:2002;1789. and references therein
28. List B., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 122:2000;2395
29. Sakthivel K., Notz W., Bui T., Barbas C.F. III. J. Am. Chem. Soc. 123:2001;5260
30. Zhong G., Lerner R.A., Barbas C.F. III. Angew. Chem., Int. Ed. 38:1999;3738