Highly Stereoselective Aldol Reactions by Memory of Chirality: Synthesis of Quaternary β‐Hydroxy α‐Amino Acids.

Autor:	Roupnel, Loïc, Guillot, Régis, Gori, Didier, Viswambharan, Baby, Kouklovsky, Cyrille, Alezra, Valérie
Zdroj:	Helvetica Chimica Acta; Oct2021, Vol. 104 Issue 10, p1-15, 15p
Abstrakt:	We describe here an asymmetric aldol reaction based on the principle of Memory of Chirality. From α‐amino acids such as leucine and methionine, we have synthesized in two steps quaternary α‐amino acid derivatives with high diastereoselectivity and enantioselectivity, using the chirality of the initial α‐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 β‐hydroxy α‐amino acids after acidic hydrolysis. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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