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

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

Vannapha Pharikronburee,^a Teerachai Punirun,^a Darunee Soorukram,^a Chutima Kuhakarn,^a Patoomratana Tuchinda,^a Vichai Reutrakul^a and Manat Pohmakotr*^a

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* Corresponding authors

^a Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
E-mail: manat.poh@mahidol.ac.th
Fax: +66 2 644 5126
Tel: +66 2 201 5158

Abstract

PhSCF₂SiMe₃ (1) 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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Article information

DOI: https://doi.org/10.1039/C3OB27193E
Article type: Paper
Submitted: 08 Nov 2012
Accepted: 07 Jan 2013
First published: 09 Jan 2013

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Org. Biomol. Chem., 2013,11, 2022-2033

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

V. Pharikronburee, T. Punirun, D. Soorukram, C. Kuhakarn, P. Tuchinda, V. Reutrakul and M. Pohmakotr, Org. Biomol. Chem., 2013, 11, 2022 DOI: 10.1039/C3OB27193E

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Organic & Biomolecular Chemistry