Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

Horino, Yoshikazu; Aimono, Ataru; Minoshima, Naoki; Abe, Hitoshi

doi:10.1016/j.tetlet.2016.06.121

Cited by 5 publications

(1 citation statement)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Taking advantage of triethylborane as a Lewis acid, which is capable of coordinating to the hydroxy group to increase its leaving group capability, a palladium-catalyzed three-component reaction using B(pin)-substituted allyl alcohols was attempted, and similar results were obtained in many cases (Scheme 19). [41] Scheme 18. Palladium-catalyzed three-component reaction involving sp 2 À sp 3 coupling.…”

Section: Diastereoselective Synthesis Of Homoaldol Equivalent Productsmentioning

confidence: 99%

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Horino

Korenaga

2021

The Chemical Record

Self Cite

View full text Add to dashboard Cite

π-Allylpalladium complexes can not only serve as electrophilic allylating agents for a broad range of nucleophiles, but also nucleophilic allylating agents for electrophiles depending on their electronic environments. In contrast to these typical reactivities of π-allylpalladium complexes, silylated and borylated π-allylpalladium species show unique reactivities that can allow versatile transformations in addition to simple allylation. Herein, four different types of transformations that are in principle achieved via the inherently reactive silylated and borylated π-allylpalladium species as common intermediates are described. An appropriate selection of ligands of the silylated and borylated π-allylpalladium species can allow control over the reaction pathways.

show abstract

Section: Diastereoselective Synthesis Of Homoaldol Equivalent Productsmentioning

confidence: 99%