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Literature DB >> 23763240

Design of chiral bifunctional quaternary phosphonium bromide catalysts possessing an amide moiety.

Seiji Shirakawa¹, Takashi Tokuda, Atsuyuki Kasai, Keiji Maruoka.

Abstract

Novel bifunctional quaternary phosphonium bromides possessing an amide moiety were designed for the highly enantioselective sulfenylation and chlorination of β-ketoesters under base-free phase-transfer conditions. The tuning of an amide moiety of the catalyst was crucial to achieve high reactivity and enantioselectivity.

Entities: Chemical

Year: 2013 PMID： 23763240 DOI： 10.1021/ol4013926

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts.

Authors: Maciej Majdecki; Piotr Grodek; Janusz Jurczak
Journal: J Org Chem Date: 2020-12-15 Impact factor: 4.354

2. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF₃S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Authors: Andreas Eitzinger; Jan Otevrel; Victoria Haider; Antonio Macchia; Antonio Massa; Kirill Faust; Bernhard Spingler; Albrecht Berkessel; Mario Waser
Journal: Adv Synth Catal Date: 2021-02-17 Impact factor: 5.837

Design of chiral bifunctional quaternary phosphonium bromide catalysts possessing an amide moiety.

1. Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts.

2. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF₃S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Review 3. Beyond a solvent: triple roles of dimethylformamide in organic chemistry.

4. Catalytic, enantioselective sulfenylation of ketone-derived enoxysilanes.

Review 5. Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Design of chiral bifunctional quaternary phosphonium bromide catalysts possessing an amide moiety.

1. Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts.

2. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Review 3. Beyond a solvent: triple roles of dimethylformamide in organic chemistry.

4. Catalytic, enantioselective sulfenylation of ketone-derived enoxysilanes.

Review 5. Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

2. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF₃S-, 3-RS-, and 3-F-Substituted Isoindolinones.