Article Dans Une Revue Asian Journal of Organic Chemistry Année : 2024

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

Résumé

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.

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Chimie organique
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Dates et versions

hal-04813588 , version 1 (02-12-2024)

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Thomas Defuentes, Jérôme Lhoste, Catherine Gaulon-Nourry, Anne‐sophie Castanet, Anne‐caroline Chany. Access to Syn α‐Amino‐β‐Hydroxyesters by N−H Insertion on O‐Protected α‐Diazo‐β‐Hydroxyesters. Asian Journal of Organic Chemistry, In press, ⟨10.1002/ajoc.202400539⟩. ⟨hal-04813588⟩
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