Highly stereoselective aldol reactions by Memory of Chirality: synthesis of quaternary beta-hydroxy alpha-amino acids
- Resource Type
- Authors
- Didier Gori; Régis Guillot; Loïc Roupnel; Baby Viswambharan; Valérie Alezra; Cyrille Kouklovsky
- Source
- Helvetica Chimica Acta
Helvetica Chimica Acta, 2021, 104 (10), ⟨10.1002/hlca.202100127⟩
- Subject
- chemistry.chemical_classification
Memory of Chirality
Stereochemistry
organic chemicals
Tertiary Aromatic Amide
Organic Chemistry
asymmetric synthesis
Enantioselective synthesis
Biochemistry
Catalysis
Amino acid
Inorganic Chemistry
Aldol reaction
chemistry
Drug Discovery
polycyclic compounds
[CHIM]Chemical Sciences
Stereoselectivity
Physical and Theoretical Chemistry
Chirality (chemistry)
- Language
- English
- ISSN
- 0018-019X
1522-2675
International audience; 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 quaternarybeta-hydroxy alpha-amino acids after acidic hydrolysis.