Palladium‐Catalyzed Three‐Component Reaction of 3‐(Tri‐<i>n</i>‐ butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ‐Substituted Allylic Tin Reagents

Horino, Yoshikazu; Sugata, Miki; Abe, Hitoshi

doi:10.1002/adsc.201501049

Cited by 9 publications

(5 citation statements)

References 70 publications

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“…To overcome such limitations, we reported that catalytically generated allylic heterobimetallic species such as allylic Pd/boryl and Pd/stannyl species are useful intermediates for the umpolung allylation of aldehydes to provide ( Z )- and ( E )-homoallylic alcohols, respectively, with good to high stereoselectivity . However, such methods require the independent preparation of different starting materials.…”

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confidence: 99%

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

et al. 2017

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Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α,γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

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confidence: 99%

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

et al. 2017

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“…The three-component reaction of B(pin)-substituted allyl acetates, aldehydes, and triorganoboranes proceeded successfully (Scheme 18). [40] This method was compatible with various aldehydes, which could be problematic in the metal-catalyzed allylation reaction of aldehydes. For example, 4-and 2-hydroxybenzaldehydes were used without prior protection of the hydroxyl group.…”

Section: Diastereoselective Synthesis Of Homoaldol Equivalent Productsmentioning

confidence: 97%

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Horino

Korenaga

2021

The Chemical Record

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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.

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“…Moderate diastereoselectivities were also observed for heteroaryl substrates. Previous studies of Horino and co-workers had also demonstrated the formation of (Z)-anti-homoallylic alcohol, but in this case, using 3-(pinacolatoboryl) allyl acetates, aldehydes, and triorganoboranes under the influence of a Pd-PCyPh 2 catalyst system (Horino, Sugata & Abe, 2016).…”

Section: Scheme XII Reaction System For the Synthesis Of Allylic Alcmentioning

confidence: 81%

“…2016 has also been a productive year in the field as yet another study for the facile process of (E)-antihomoallylic alcohol production was developed using a palladium-xantphos-catalyzed reaction system of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes (Scheme XI) (Horino, Sugata & Abe, 2016). This served as alternative to the typical carbonyl allylation bound with the limitation of introducing n-alkyl, sec-alkyl, and aryl groups, which came from triorganoboranes, into the alkene.…”

Section: Scheme XII Reaction System For the Synthesis Of Allylic Alcmentioning

confidence: 99%

Palladium-Catalyzed Carbonyl Allylation Reactions Using Tin Chloride: A Mini-Review

Guidote

Baltazar

Yanela

et al. 2018

KIMIKA

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The treatment of allylic alcohols as synthons of carbanions for carbonyl allylation reactions in the presence of a Pd-SnCl2 system has been one of the most interesting and most useful developments demonstrated by Yoshiro Masuyama and co-workers in the field of organic synthesis. The reaction makes use of palladium as an effective catalyst and tin (II) chloride as a low-valent reducing agent which also effectively transforms the allylic group to a nucleophilic group. The organic, as well as organometallic, chemistry of how the transformations occur and how the metals take part in the reaction is of great interest. These could help allow for better optimization of reagents and solvents, for better control of the extent of reaction or yield of desired product, and for possible applications in other reaction systems. This review will focus primarily on the work of Yoshiro Masuyama and various co-workers on carbonyl allylation reactions making use of a Pd-SnCl2 system or substitutes thereof.

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Palladium‐Catalyzed Three‐Component Reaction of 3‐(Tri‐n‐ butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ‐Substituted Allylic Tin Reagents

Abstract: The reaction tolerates 1‐aryl as well as 1‐hetaryl substituted 3‐(tri‐n‐butylstannyl)allyl acetates, aryl, hetaryl, alkenyl as well as alkyl aldehydes and various boranes.

Cited by 9 publications

References 70 publications

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Versatile Reactivity of Metalloid‐Substituted π‐Allylpalladium Species

Palladium-Catalyzed Carbonyl Allylation Reactions Using Tin Chloride: A Mini-Review

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