A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide

Angewandte Chemie - International Edition

Volumn 44, Issue 9, 2005, Pages 1378-1382

  Nicolaou, K C ^a,b   Estrada, Anthony A ^a,b   Zak, Mark ^a,b   Lee, Sang Hyup ^a,b   Safina, Brian S ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Epimerization; Hydrolysis; Synthetic methods; Tin

Indexed keywords

CARBOXYLIC ACIDS; HYDROLYSIS; REACTION KINETICS; STEREOCHEMISTRY;

ELIMINATION REACTIONS; EPIMERIZATION; STREOCHEMICAL INTEGRITY; TRIMETHYLTIN HYDROOXIDE;

ESTERS;

1,2 DICHLOROETHANE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; TRIMETHYLTIN; TRIMETHYLTIN HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELIMINATION REACTION; EPIMERIZATION; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

CHEMISTRY, ORGANIC; ESTERS; HYDROLYSIS; MOLECULAR STRUCTURE; TRIMETHYLTIN COMPOUNDS;

EID: 14844299308     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462207     Document Type: Article

References (25)

1. a) K. C. Nicolaou, B. S. Safina, M. Zak, A. A. Estrada, S. H. Lee, Angew. Chem. 2004, 116, 5197-5202; Angew. Chem. Int. Ed. 2004, 43, 5087-5092;
2. a) K. C. Nicolaou, B. S. Safina, M. Zak, A. A. Estrada, S. H. Lee, Angew. Chem. 2004, 116, 5197-5202; Angew. Chem. Int. Ed. 2004, 43, 5087-5092;
3. b) K. C. Nicolaou, M. Zak, B. S. Safina, S. H. Lee, A. A. Estrada, Angew. Chem. 2004, 116, 5202-5207; Angew. Chem. Int. Ed. 2004, 43, 5092-5097.
4. b) K. C. Nicolaou, M. Zak, B. S. Safina, S. H. Lee, A. A. Estrada, Angew. Chem. 2004, 116, 5202-5207; Angew. Chem. Int. Ed. 2004, 43, 5092-5097.
5. a) R. L. E. Furlan, E. G. Mata, O. A. Mascaretti, J. Chem. Soc. Perkin Trans. 1 1998, 355-358;
6. b) R. L. E. Furlan, E. G. Mata, O. A. Mascaretti, C. Pena, M. P. Coba, Tetrahedron 1998, 54, 13023-13034;
7. c) R. L. E. Furlan, O. A. Mascaretti, Aldrichimica Acta 1997, 30, 55-69;
8. d) R. L. E. Furlan, E. G. Mata, O. A. Mascaretti, Tetrahedron Lett. 1996, 37, 5229-5232.
9. For a related process that employs dibutyltin oxide to induce transesterifications, see: P. Baumhof, R. Mazitschek, A. Giannis, Angew. Chem. 2001, 113, 3784-3786; Angew. Chem. Int. Ed. 2001, 40, 3672-3674.
10. For a related process that employs dibutyltin oxide to induce transesterifications, see: P. Baumhof, R. Mazitschek, A. Giannis, Angew. Chem. 2001, 113, 3784-3786; Angew. Chem. Int. Ed. 2001, 40, 3672-3674.
11. K. C. Nicolaou, M. Nevalainen, M. Zak, S. Bulat, M. Bella, B. S. Safina, Angew. Chem. 2003, 115, 3540-3546; Angew. Chem. Int. Ed. 2003, 42, 3418-3424.
12. K. C. Nicolaou, M. Nevalainen, M. Zak, S. Bulat, M. Bella, B. S. Safina, Angew. Chem. 2003, 115, 3540-3546; Angew. Chem. Int. Ed. 2003, 42, 3418-3424.
13. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
14. C. J. Salomon, G. O. Danelon, O. A. Mascaretti, J. Org. Chem. 2000, 65, 9220-9222.
15. Arylglycine derivatives such as 22 are known to be extremely prone to racemization; for examples, see: a) H. Deng, J.-K. Jung, T. Liu, K. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 9032-9034;
16. b) F. A. Davis, D. L. Fanelli, J. Org. Chem. 1998, 63, 1981-1985;
17. c) A. J. Pearson, G. Bignan, P. Zhang, M. Chelliah, J. Org. Chem. 1996, 61, 3940-3941;
18. d) A. J. Pearson, H. Shin, J. Org. Chem. 1994, 59, 2314-2323.
19. a) A. J. Pearson, M. V. Chelliah, G. C. Bignan, Synthesis 1997, 5, 536-540;
20. b) L. B. Crast, US Patent 3489750, 1970 [Chem. Abstr. 1970, 72, 100725].
21. b) L. B. Crast, US Patent 3489750, 1970 [Chem. Abstr. 1970, 72, 100725].
22. a) J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549;
23. b) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
24. a) I. A. Motorina, C. Huel, E. Quiniou, J. Mispelter, E. Adjadj, D. S. Grierson, J. Am. Chem. Soc. 2001, 123, 8-17;
25. b) F. Polyak, W. D. Lubell, J. Org. Chem. 2001, 66, 1171-1180.