Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 30, Pages 10711-10718Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9039604
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- Universite de Paris-Sud
- CNRS
- Ministere de l'Enseignement Superieur et dela Recherche
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A new methodology for the asymmetric synthesis of quaternary a-substituted amino acids using memory of chirality has been developed. The strategy utilizes the dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an alpha-amino acid during an enolization step. Starting from five different L-amino acids, the corresponding oxazolidin-5-ones containing a tertiary aromatic amide group have been synthesized in one step and then alkylated with various electrophiles, with good yields and enantioselectivities (up to 96% and up to > 99% after recrystallization). One-step deprotection affords enantioenriched or enantiopure quaternary alpha-amino acids. We describe here the optimization process, the results obtained in each series and a plausible explanation, based on NMR studies, DFT calculations and crystallographic structures. The methodology presented herein constitutes an efficient synthesis of enantiopure quaternary alpha-amino acids (three steps only) starting from tertiary L-amino acids, without any external source of chirality.
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