Synthesis of <i>cis</i>-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

Saborit, Gisela V.; Cativiela, Carlos; Jiménez, Ana I.; Bonjoch, Josep; Bradshaw, Ben

doi:10.3762/bjoc.14.237

Cited by 5 publications

(1 citation statement)

References 36 publications

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“…In 2018, a novel method using the Danheiser annulation was developed to synthesize cis-hydrindan-2,4-diones that could further be used for the synthesis of lycopodium alkaloids. 40 The use of allenylsilanes as 1,3-dipoles was extended to other cycloadditions. Under Lewis acidic conditions cyclopropanes 47 can serve as 1,3-dipolar synthons and participate in cycloaddition reactions with allenylsilanes 48 (Scheme 6…”

Section: Scheme 5 Cyclopentene Annulation Reaction; the Danheiser Annmentioning

confidence: 99%

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Beļaunieks

Puriņš²,

Turks³

2020

Synthesis

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Many chemical transformations of organosilicon compounds proceed due to the capability of silyl substituents to stabilize a positive charge in its β-position. This short review provides an overview of the present understanding of the β-silicon effect and focusses on the synthetic applications of 1,2-silyl shifts resulting from non-vertical stabilization of alkylcarbenium ions and vinyl cations. The reactions of silicon containing unsaturated starting materials, alkenes, allenes, and alkynes, involving β-silyl group stabilized cationic intermediates, transition metal carbenes, or vinylidene complexes will be discussed.1 Introduction2 Origins of the β-Silicon Effect3 Reactions of Allenylsilanes4 Reactions of Alkynes4.1 Propargylsilanes4.2 Alkynylsilanes5 Reactions of Alkenes5.1 Allylsilanes5.2 Vinylsilanes6 Conclusions

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Section: Scheme 5 Cyclopentene Annulation Reaction; the Danheiser Annmentioning

confidence: 99%

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Beļaunieks

Puriņš²,

Turks³

2020

Synthesis

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Miscellaneous Reactions

2020

Applied Organic Chemistry

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Strategic Applications of the β‐Silicon Effect

Roberts

McLaughlin

2022

Adv Synth Catal

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Organosilicon reagents are highly versatile and privileged scaffolds in modern synthetic chemistry, largely due to the range of transformations the groups are amenable to. The β‐Silicon effect is one of the fundamental phenomena underpinning the inherent reactivity of organosilicon reagents, allowing unsaturated organosilanes to undergo a range of electrophilic substitutions with a variety of nucleophiles. The application of the β‐Silicon effect in a range of organic transformations is reviewed with the discussion divided up based on the class of silane. The reactivity of these compounds towards carbon, heteroatom and metallic electrophiles is discussed from classical applications such as the Sakurai allylation to contemporary applications such as cross‐coupling chemistry. In addition, examples of these transformations in the context of methodology development and natural product synthesis are provided.

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Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

Cited by 5 publications

References 36 publications

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Miscellaneous Reactions

Strategic Applications of the β‐Silicon Effect

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