Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of γ-difluoromethylated γ-lactams

PhSCF2SiMe3 () underwent fluoride-catalyzed nucleophilic addition to the carbonyl group of anhydrides to provide the corresponding γ-difluoro(phenylsulfanyl)methyl γ-lactols, which were employed for the synthesis of γ-difluoromethylated γ-lactams.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-03, Vol.11 (12), p.2022-2033
Main Authors: Pharikronburee, Vannapha, Punirun, Teerachai, Soorukram, Darunee, Kuhakarn, Chutima, Tuchinda, Patoomratana, Reutrakul, Vichai, Pohmakotr, Manat
Format: Article
Language:English
Subjects:
Anhydrides - chemistry
Catalysis
Fluorides - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Sulfides - chemistry
Trimethylsilyl Compounds - chemistry
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Description
Summary:PhSCF2SiMe3 () underwent fluoride-catalyzed nucleophilic addition to the carbonyl group of anhydrides to provide the corresponding γ-difluoro(phenylsulfanyl)methyl γ-lactols, which were employed for the synthesis of γ-difluoromethylated γ-lactams.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob27193e