Journal
TETRAHEDRON
Volume 72, Issue 13, Pages 1706-1715Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.02.027
Keywords
Short alpha/beta-peptide; Bicyclic beta-amino acid; Organocatalysis; Asymmetric aldol reaction
Categories
Funding
- Centre National de la Recherche Scientifique
- MESR
Ask authors/readers for more resources
A series of N-pyrrolidine-based alpha,beta-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2] octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording beta-hydroxy ketones in high yields and good enantioselectivities (up to 87%). (C) 2016 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available