Carboxylate catalysis: a mild catalytic O-silylative aldol reaction of aldehydes and ethyl diazoacetate

16 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

aldol reaction
silylation
carboxylate catalysis
diazo compounds
protecting groups

Supplementary materials

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Supporting Information
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Copies of NMR spectra, SFC chromatograms and details of competition experiments
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