The Synthesis of Trimethylsilylmethyl Allylic Sulfones

Harmata, Michael; Herron, Barry F.

doi:10.1055/s-1993-25828

Cited by 17 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cycloaddition precursors for this work were easily prepared by the addition of the appropriate cuprates to the corresponding sulfonyl allenes, as exemplified by the synthesis of 59. 19 Attempts to directly alkylate the cuprate addition product were not successful. We also failed at attempts to alkylate 60 via a deprotonation-alkylation sequence.…”

Section: Trimethylsilylmethyl Allylic Sulfones and Alcoholsmentioning

confidence: 99%

Exploration of Fundamental and Synthetic Aspects of the Intramolecular 4 + 3 Cycloaddition Reaction

Harmata

2001

Acc. Chem. Res.

Self Cite

198

View full text Add to dashboard Cite

In this Account, a summary of our work in the exploration and development of intramolecular 4 + 3 cycloaddition reactions between dienes and allylic cations is presented. Alkoxyallylic sulfones are useful precursors for the generation of allylic cations which are good dienophiles. Such substrates allowed a number of important pieces of data concerning the cycloaddition to be obtained. The evolution of the work has involved pursuing other methods for allylic cation generation, an investigation of stereochemical variables and applications, including the total syntheses of aphanamol I, widdrol, and (+)-dactylol.

show abstract

Section: Trimethylsilylmethyl Allylic Sulfones and Alcoholsmentioning

confidence: 99%

Exploration of Fundamental and Synthetic Aspects of the Intramolecular 4 + 3 Cycloaddition Reaction

Harmata

2001

Acc. Chem. Res.

Self Cite

198

View full text Add to dashboard Cite

show abstract

“…(Trimethylsilyl)methyl allylic sulfones were investigated as part of our plan to explore and expand the scope of the application of allylic sulfones in the 4 + 3 cycloaddition reaction. The preparation of (trimethylsilyl)methyl allylic sulfones is a simple process involving cuprate addition to the appropriate allenes . Further elaboration via deprotonation and alkylation makes substrates for intramolecular 4 + 3 cycloadditions readily available …”

mentioning

confidence: 99%