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

Janssens Julien | Zendy; Berionni Guillaume | Zendy; Robiette Raphaël | Zendy

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

Author(s) -

Janssens Julien,

Berionni Guillaume,

Robiette Raphaël

Publication year - 2025

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202500033

Subject(s) - chemoselectivity , chemistry , wittig reaction , organic chemistry , boron , combinatorial chemistry , catalysis

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

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