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Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity

Year: 2025

Type: article

Abstract: We report our results on the development of the Peterson olefination using gem‐borylsilylmethane derivatives to synthesize di‐ and tri‐substituted vinyl boronates. We show that the electronic properties of the carbonyl partner have no effect on the Peterson/boron‐Wittig chemoselectivity whereas the nature of the silane group plays an important role. A DFT study helps explain observed reactivity, chemoselectivity and stereoseletivity

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500033

Authors: Julien Janssens, Guillaume Berionni, Raphaël Robiette

Institutions: UCLouvain, University of Namur, Namur Institute of Structured Matter

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W4407191587

FWCI: 0.894

Cites: 36

Cited by: 3

Related to: 10