Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins

doi:10.1021/JO9805652

Paper

Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins

Published Jul 10, 1998 · Michael D. Groaning, G. P. Brengel, A. Meyers

Journal of Organic Chemistry

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Abstract

Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Some preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.

Study Snapshot

Allyldimethyltritylsilane effectively synthesizes various cyclopentanols, oxetanes, and tetrahydrofurans by reacting with electron deficient olefins, providing a variety of organic compounds.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins

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References

Citations

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This study presents a general method for generating allyl carbenium ions from propargyl silanes, leading to silyl dienes and silyl indenes, with potential applications in various reactions.

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Nickel-catalyzed reductive [2+2] cyclobutene synthesis with primary aminophosphine ligand enables the synthesis of tetrasubstituted cyclobutenes from alkynes, with potential applications in synthesis of epi-tru

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Nickel hydrosilylation catalysts efficiently catalyze alkene hydrosilylation under ambient conditions, with potential applications in industrially important reactions such as siloxy-, amino-, and epoxy-substituted alkenes.

A review on green Lewis acids: zirconium(IV) oxydichloride octahydrate (ZrOCl2·8H2O) and zirconium(IV) tetrachloride (ZrCl4) in organic chemistry

Green Lewis acids, ZrCl4 and ZrOCl28H2O, are effective catalysts for various organic reactions due to their low toxicity, availability, handling, moisture stability, and low cost.

(Salicylaldiminato)Ni(II)-catalysts for hydrosilylation of olefins

(Salicylaldiminato)methylnickel complexes efficiently catalyze hydrosilylation of various olefins, with excellent selectivity for monohydrosilylation and high activity for secondary hydrosilanes.