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

Autor: Akhil K. Dubey, Raghunath Chowdhury
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 2642-2649 (2021)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.17.177
Popis: 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.
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