Highly stereoselective aldol reactions by Memory of Chirality: synthesis of quaternary beta-hydroxy alpha-amino acids

Loïc Roupnel (1) , Régis Guillot (1) , Didier Gori (2, 1) , Baby Viswambharan (1) , Cyrille Kouklovsky (1) , Valérie Alezra (1)

1 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
2 LCE - Laboratoire Chimie de l'environnement

We describe here an asymmetric aldol reaction based on the principle of Memory of Chirality. From -amino acids such as leucine and methionine, we have synthesized in 2 steps quaternary alpha-amino acid derivatives with high diastereoselectivity and enantioselectivity, using the chirality of the initial alpha-amino acid as the only chirality source. Furthermore, we were able to determine the relative and absolute configurations of the aldol products thanks to crystallographic structures and thus showed that the relative configuration depended on the aldehyde employed. We proposed a stereoselectivity explanation and obtained also quaternarybeta-hydroxy alpha-amino acids after acidic hydrolysis.

Mots clés: Amino acid; Memory of Chirality; Aldol reaction; asymmetric synthesis; Tertiary Aromatic Amide

Domaines: Chimie

Loïc Roupnel, Régis Guillot, Didier Gori, Baby Viswambharan, Cyrille Kouklovsky, et al.. Highly stereoselective aldol reactions by Memory of Chirality: synthesis of quaternary beta-hydroxy alpha-amino acids. Helvetica Chimica Acta, 2021, 104 (10), ⟨10.1002/hlca.202100127⟩. ⟨hal-03576201⟩