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N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis

Abstract : 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%).
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https://hal.univ-lorraine.fr/hal-01532027
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Submitted on : Friday, June 2, 2017 - 12:06:50 PM
Last modification on : Thursday, February 25, 2021 - 10:00:02 AM

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Pierre Milbeo, Kelly Maurent, Laure Moulat, Aurelien Lebrun, Claude Didierjean, et al.. N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis. Tetrahedron, Elsevier, 2016, 72 (13), pp.1706-1715. ⟨10.1016/j.tet.2016.02.027⟩. ⟨hal-01532027⟩

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