Bifunctional phase-transfer catalysts for synthesis of 2-oxazolidinones from isocyanates and epoxides

Cui, Dai; Li, Yuedan; Huang, Ping; Tian, Zhuang; Jia, Yi‐Xia; Wang, Ping-An

doi:10.1039/d0ra00693a

Cited by 9 publications

(2 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Encouraged by the report of Toda et al using a bifunctional phosphonium salt catalyst, Cui and coworkers examined the effects of bifunctional tetraalkylammonium bromide catalysts possessing a urea moiety (Scheme 12). 32 The urea moiety on the ammonium bromide catalyst functions as a hydrogen-bonding donor to activate epoxide substrates. 33,34 An optimized bifunctional ammonium bromide catalyst could efficiently promote the reaction of glycidyl ethers and aryl isocyanates to provide corresponding 2-oxazolidinone products 1 in good to high yields.…”

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

et al. 2022

View full text Add to dashboard Cite

Although the wide variety of heterocyclic compounds is common knowledge, chiral 2‐oxazolidinones are recognized as some of the most important heterocycles in medicinal chemistry. Many important pharmaceutical molecules have been constructed based on the chiral 2‐oxazolidinone backbone. Therefore, the development of even more efficient catalytic methods for the synthesis of chiral 2‐oxazolidinones remains a very important pursuit in the field of synthetic organic chemistry. This review summarizes the coupling reactions of epoxides and isocyanates for the preparation of 2‐oxazolidinones. Both metal catalysts and organocatalysts promote these reactions. Optically pure 2‐oxazolidinones are prepared from optically pure epoxide substrates via these catalytic methods. A synthetic example of a commercially available pharmaceutical compound utilizing this method is also introduced.

show abstract

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The most common of those units include the hydroxyl group, amide, (thio)urea and squaramide. In the case of quaternary onium salts, there are many examples for the installation of these units into catalyst scaffold [15][16][17][18][19][20]. However, in crown ether derivatives, only hydroxyl groups are frequently used as ancillary components capable of forming hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Crown Ether-Squaramides and Their Application as Phase-Transfer Catalysts

et al. 2021

View full text Add to dashboard Cite

This work presents the synthesis of six new phase-transfer organocatalysts in which the squaramide unit is directly linked to the nitrogen atom of an aza-crown ether. Four chiral skeletons, namely hydroquinine, quinine, cinchonine (cinchonas), and α-d-glucopyranoside were responsible for the asymmetric construction of an all-carbon quaternary stereogenic center in α-alkylation and Michael addition reactions of malonic esters. We investigated the effects of these different chiral units and that of crown ethers with different sizes on catalytic activity and enantioselectivity. During extensive parameter investigations, both conventional and emerging green solvents were screened, providing valuable α,α-disubstituted malonic ester derivatives with excellent yields (up to 98%).

show abstract

Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Lin,

Chang,

Chiou

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

The method for converting epoxy carbamates to oxazolidinones is outlined in this study. This innovative approach combines intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, thereby facilitating rapid conversion. Significantly, this method effectively addresses challenges associated with the use of expensive reagents, harsh reaction conditions, and prolonged reaction times, presenting a more efficient alternative. Demonstrating favorable reactivity across a diverse range of aryl groups, as well as benzyl or tert‐butyl carbamates, the method consistently yields satisfactory results, with oxazolidinone formation ranging from 55% to 99% in over 24 examples. The synthesized oxazolidinones, including 5v–5x, hold substantial promise as intermediates for the synthesis of crucial synthetic molecules. Furthermore, the versatility of this method is underscored by its successful application in the formation of the 6‐membered ring 1,3‐oxazinan‐2‐one. These findings not only contribute to the advancement of synthetic methodologies but also pave the way for a streamlined synthesis of important pharmaceutical compounds.

show abstract

Bifunctional phase-transfer catalysts for synthesis of 2-oxazolidinones from isocyanates and epoxides

Abstract: A series of bifunctional phase-transfer catalysts were synthesized to catalyze the [3 + 2] coupling reaction of isocyanates and epoxides to afford 2-oxazolidinones in good to high yields (up to 92% yield) using PhCl as a solvent at 100 °C within 12 h.

Cited by 9 publications

References 32 publications

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

Synthesis of Novel Crown Ether-Squaramides and Their Application as Phase-Transfer Catalysts

Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Contact Info

Product

Resources

About