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The Deazidoalkoxylation: Sequential Nucleophilic Substitutions With Diazidated Diethyl Malonate

Phillip Biallas, Tobias M Mensak, Kevin-Alexander Kunz, Stefan F Kirsch

J Org Chem. 2019 Feb 1;84(3):1654-1663.

PMID: 30676025

Abstract:

Diazidated malonamides derived from amines and diazidated diethyl malonate react with lithiated alcohols through nucleophilic substitution reactions where azide acts as an unconventional leaving group. This deazidoalkoxylation leads to the formal construction of N, O-acetals, and the remaining azide functionality is a useful entry point for further functionalizations through, for example, standard cycloaddition chemistry. Thus, the presented chemistry provides an easy route toward densely functionalized molecules: Amines, alcohols, and alkynes can be attached onto the small malonate core unit in a sequential manner.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP105533 Diethyl malonate Diethyl malonate 105-53-3 Price
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