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A practical method for selective cleavage of a tert-butoxycarbamoyl N-protective group from N,N-diprotected α-amino acid derivatives using Montmorillonite K-10

AuthorsHernández, J. Nicolás; Pinacho Crisóstomo, Fernando R. ; Martín, Tomás ; Martín, Víctor S.
Keywordsα-Amino acids
Heterogeneous catalyst
Protecting groups
Asymmetric synthesis
Issue Date8-Aug-2007
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry 30: 5050-5058 (2007)
AbstractA new, practical, and mild procedure for the selective cleavage of a tert-butoxycarbonyl group (Boc) in N-Boc-N-acyl-diprotected amines is described. When applied to α-amino acids, complete integrity of the stereochemistry was observed. The use of N,N-di-Boc-α-amino-δ- and γ-hydroxy esters provided both δ- and γ-lactones in very good yields. The method is based on the use of Montmorillonite K-10 either in CH2Cl2 at room temperature or in toluene at 65°C and is compatible with the presence of a large range of functional and other protecting groups in the substrates. In most cases virtually pure samples are obtained after filtration and removal of solvents.
Description9 pages, 3 tables, 1 scheme.-- Supporting information (26 pages) available at: http://www.wiley-vch.de/contents/jc_2046/2007/o200700296_s.pdf
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.200700296
Appears in Collections:(IPNA) Artículos
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