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

Vannapha Pharikronburee; Teerachai Punirun; Darunee Soorukram; Chutima Kuhakarn; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr

doi:10.1039/c3ob27193e

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

Org Biomol Chem. 2013 Mar 28;11(12):2022-33. doi: 10.1039/c3ob27193e. Epub 2013 Feb 6.

Authors

Vannapha Pharikronburee¹, Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr

Affiliation

¹ Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.

PMID: 23386230
DOI: 10.1039/c3ob27193e

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anhydrides / chemistry*
Catalysis
Fluorides / chemistry*
Lactams / chemical synthesis*
Lactams / chemistry
Molecular Structure
Sulfides / chemistry*
Trimethylsilyl Compounds / chemistry*

Substances

Anhydrides
Lactams
Sulfides
Trimethylsilyl Compounds
Fluorides