Work

Access to Syn α‐Amino‐β‐Hydroxyesters by N−H Insertion on O‐Protected α‐Diazo‐β‐Hydroxyesters

Year: 2024

Type: article

Abstract: The N−H insertion reaction is a versatile method for creating C−N bonds under mild conditions, providing in particular an efficient access to both natural and non‐natural α‐amino acid derivatives. In this field, the direct N−H insertion on α‐diazo‐β‐hydroxyesters has not yet been investigated and constitutes a significant challenge, due to competitive migration processes. We report herein the first N−H insertions on O‐protected α‐diazo‐β‐aryl‐β‐hydroxyesters, enabling to synthesize a wide range of α‐amino‐β‐hydroxyesters by tuning the nature of the amine and the aryl substituent. Overall, 28 N−H insertion products have been isolated, with moderate to good yields in most cases, and diastereoisomeric ratios up to 8.0 : 1 in favor of the syn diastereoisomer.

Source: Asian Journal of Organic Chemistry

DOI: 10.1002/ajoc.202400539

Authors: Thomas Defuentes, Jérôme Lhoste, Catherine Gaulon‐Nourry, Anne‐Sophie Castanet, Anne‐Caroline Chany

Institutions: Centre National de la Recherche Scientifique, Le Mans Université, Institut des Molécules et Matériaux du Mans

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,840

Funder: Agence Nationale de la Recherche