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Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions.

ABSTRACT: An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.

SUBMITTER: Dubey AK

PROVIDER: S-EPMC8561140 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions.

Dubey Akhil K AK Chowdhury Raghunath R

Beilstein journal of organic chemistry 20211027

An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized r ...[more]

PMID: 34795801

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