Selective Formal Transesterification of Fluorinated 2-(Trimethylsilyl)ethyl α-Imino Esters Mediated by TBAF

6533b852fe1ef96bd12ab7c1

RESEARCH PRODUCT

Selective Formal Transesterification of Fluorinated 2-(Trimethylsilyl)ethyl α-Imino Esters Mediated by TBAF

Santos Fustero Carlos Del Pozo Amador Garcia Silvia Catalan Vanessa Rodrigo María Sánchez-roselló

subject

chemistry.chemical_classification Trimethylsilyl Chemistry Organic Chemistry chemistry.chemical_element Transesterification Chemical synthesis Reaction rate chemistry.chemical_compound Electrophile Fluorine Organic chemistry heterocyclic compounds Selectivity Alkyl

description

The scope of the transesterification reaction between beta-fluorinated alpha-imino esters and various electrophiles in the presence of TBAF as fluorine source is described. The reaction is highly selective for alkyl iodides, bromides, and mesylates, while alkyl chlorides react at a significantly slower rate and tosylates do not react under the reaction conditions. This methodology represents a simple and useful alternative for the preparation of a wide variety of fluorinated alpha-imino esters.

year	journal	country	edition	language
2008-06-21	The Journal of Organic Chemistry

https://doi.org/10.1021/jo800567a

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