What question did this study set out to answer?

Investigate the direct electrophilic alpha-hydroxylation of carbonyl enolates using 2-sulfonyloxaziridines to synthesize acyloins.

August 1, 1984The Journal of Organic Chemistry

Synthesis of .alpha.-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines

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Authors

FDFranklin A. DavisTemple University LVL. C. VISHWAKARMADrexel University JBJoanne G. Billmers

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Implication

Experimental study demonstrates direct oxidation of enolates to acyloins using 2-sulfonyloxaziridines, indicating an efficient synthetic route for alpha-hydroxycarbonyl compounds.

Key Points

Investigate the direct electrophilic alpha-hydroxylation of carbonyl enolates using 2-sulfonyloxaziridines to synthesize acyloins.
Generated metal enolates from carbonyl precursors under inert, low-temperature conditions.
Treated the generated enolate intermediates with 2-sulfonyloxaziridines to induce oxygen transfer.
Isolated and characterized the resulting alpha-hydroxycarbonyl products.
Demonstrated that 2-sulfonyloxaziridines selectively transfer oxygen directly to enolate carbons under mild reaction conditions.
Provided an effective synthetic method for preparing diverse alpha-hydroxycarbonyl compounds (acyloins) without requiring overoxidation or harsh reagents.

Cite This Study

Davis et al. (1984) studied this question.

synapsesocial.com/papers/6a984af755a55e94cce3702d https://doi.org/10.1021/jo00191a048

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Implication

Experimental study demonstrates direct oxidation of enolates to acyloins using 2-sulfonyloxaziridines, indicating an efficient synthetic route for alpha-hydroxycarbonyl compounds.

Synthesis of .alpha.-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines

Discussion

Member takes

Implication

Key Points

Cite This Study

Synthesis of .alpha.-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines

Discussion

Member takes

Implication

Key Points

Cite This Study

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