An Asymmetric Allylic Alkylation–Smiles Rearrangement–Sulfinate Addition Sequence to Construct Chiral Cyclic Sulfones

An Asymmetric Allylic Alkylation–Smiles Rearrangement–Sulfinate Addition Sequence to Construct Chiral Cyclic Sulfones

An asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates and β-keto sulfones was investigated by the catalysis of modified cinchona alkaloids, whose products underwent a Smiles rearrangement–sulfinate addition cascade to furnish highly functionalized five-membered cyclic sulfones in mode...

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Veröffentlicht in:Organic letters 2013-09, Vol.15 (18), p.4786-4789
Hauptverfasser: Wang, Quan-Gang, Zhou, Qing-Qing, Deng, Jin-Gen, Chen, Ying-Chun
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Allyl Compounds - chemistry
Carbonates - chemistry
Catalysis
Cinchona Alkaloids - chemistry
Molecular Structure
Stereoisomerism
Sulfones - chemical synthesis
Sulfones - chemistry
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Zusammenfassung:An asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates and β-keto sulfones was investigated by the catalysis of modified cinchona alkaloids, whose products underwent a Smiles rearrangement–sulfinate addition cascade to furnish highly functionalized five-membered cyclic sulfones in moderate to excellent enantioselectivity and good diastereoselectivity after treatment with DBU.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402158u