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Petasis boronic acid–Mannich reactions of substituted hydrazines: synthesis of α-hydrazinocarboxylic acids

✍ Scribed by David E. Portlock; Dinabandhu Naskar; Laura West; Min Li

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
93 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

N-1-(Carbamate protected)-N-2-(alkyl or aryl substituted) hydrazines can serve as amine substrates for the Petasis boronic acid-Mannich reaction, providing a practical synthetic route for the preparation of a-hydrazinocarboxylic acids. The scope and limitations of this method have been examined.

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## Abstract The mechanism of a typical Petasis‐type boronic mannich reaction (the styrylboronic acid, dibenzylamine, and __α__‐hydroxylpropionaldehyde) has been investigated using density functional theory calculations. According to our calculations, the reaction is most likely to proceed through t