title: Base-promoted C→N acyl rearrangement: an unconventional approach to α-amino acid derivatives.
abstract: We have discovered that N-alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N-protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N-alkyl α-amino acids in a very simple and reliable way.
authors: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P.O. Box 644, 48080 Bilbao (Spain).
authors: Iratxe
authors: I
authors: Ugarriza
authors: Uxue
authors: U
authors: Uria
authors: Luisa
authors: L
authors: Carrillo
authors: Jose L
authors: JL
authors: Vicario
authors: Efraim
authors: E
authors: Reyes
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002244:Carbon; D009584:Nitrogen
keywords: acyl transfer; alkylation; amino acids; rearrangements; tandem reactions