Highly efficient deacetylation by use of the neutral organotin catalyst [tBu(2)SnOH(Cl)](2)

Citation
A. Orita et al., Highly efficient deacetylation by use of the neutral organotin catalyst [tBu(2)SnOH(Cl)](2), CHEM-EUR J, 7(15), 2001, pp. 3321-3327
Citations number
51
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
7
Issue
15
Year of publication
2001
Pages
3321 - 3327
Database
ISI
SICI code
0947-6539(20010803)7:15<3321:HEDBUO>2.0.ZU;2-F
Abstract
Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu(2)SnOH(Cl)](2). The mildness of the reaction gives rise to g reat synthetic versatility and in the process a variety of functional group s are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemiz ation occurs with chiral acetyl esters. Exclusive deprotection of primary a cetyl esters in carbohydrates and nucleosides is observed. The crude produc t thus obtained can be used for further reactions without purification.