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Carboxylate Catalysis: A Catalytic O-Silylative Aldol Reaction of Aldehydes and Ethyl Diazoacetate.

ABSTRACT: A mild catalytic variant of the aldol reaction between ethyl diazoacetate and aldehydes is described using a combination of N,O-bis(trimethylsilyl)acetamide and catalytic tetramethylammonium pivalate as catalyst. The reaction proceeds rapidly at ambient temperature to afford the O-silylated aldol products in good to excellent yield, and the acetamide byproducts can be removed by simple filtration.

SUBMITTER: Riuttamaki S 

PROVIDER: S-EPMC10594658 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Carboxylate Catalysis: A Catalytic <i>O</i>-Silylative Aldol Reaction of Aldehydes and Ethyl Diazoacetate.

Riuttamäki Saara S   Bannykh Anton A   Pihko Petri M PM  

The Journal of organic chemistry 20230928 20

A mild catalytic variant of the aldol reaction between ethyl diazoacetate and aldehydes is described using a combination of <i>N</i>,<i>O</i>-bis(trimethylsilyl)acetamide and catalytic tetramethylammonium pivalate as catalyst. The reaction proceeds rapidly at ambient temperature to afford the <i>O</i>-silylated aldol products in good to excellent yield, and the acetamide byproducts can be removed by simple filtration. ...[more]

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