Highly Z-selective Julia–Kocienski Olefination Using N-sulfonylimines and Its Mechanistic Insights from DFT Calculations

08 October 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The Julia–Kocienski (JK) olefination is a reliable method for E-selective olefination; however, highly Z-selective variants are scarce. Here, we report a highly Z-selective JK olefination (with a Z ratio up to >99:1) using N-sulfonylimines as the electrophilic partners instead of aldehydes. This method showed broad substrate tolerance, accommodating various functional groups, including electron-donating/withdrawing groups, amides, halogens, carboxylic acids, and hydroxyls. DFT calculations revealed that Z-selectivity is determined mainly during the 1,2-addition step. This study enhances the toolkit for Z-selective olefination in organic synthesis.

Keywords

Julia–Kocienski olefination
Z-selective olefination

Supplementary materials

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Description
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Supporting Information
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Experimental procedures, DFT calculations, and NMR spectra
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