Jump to main content
Jump to site search

Issue 14, 2017
Previous Article Next Article

Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

Author affiliations

Abstract

A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucosamine derived 3,5-bis-(trifluoromethyl)phenyl thiourea the reaction could be accomplished with high yields (75–98%) and moderate enantioselectivities (50–64% ee). Subsequent high-yielding and racemization-free tranformations of both aromatic- and aliphatic-substituted diazene products in a one pot fashion provide a direct entry to valuable azoxy compounds and α-hydroxy-β-amino esters.

Graphical abstract: Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Feb 2017, accepted on 06 Mar 2017 and first published on 07 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00308K
Citation: Org. Biomol. Chem., 2017,15, 2993-3005
  •   Request permissions

    Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

    J. A. Carmona, G. D. Gonzalo, I. Serrano, A. M. Crespo-Peña, M. Šimek, D. Monge, R. Fernández and J. M. Lassaletta, Org. Biomol. Chem., 2017, 15, 2993
    DOI: 10.1039/C7OB00308K

Search articles by author

Spotlight

Advertisements