Preparation of a chiral hyperbranched polymer based on cinchona alkaloids and investigation of its catalytic activity in asymmetric reactions

Authors

RAFIQUL ISLAMFollow
MOHAMMAD SHAHID ULLAHFollow
ABDUS SALAMFollow
SHINICHI ITSUNOFollow

Author ORCID Identifier

RAFIQUL ISLAM: 0009-0003-5046-4751

MOHAMMAD SHAHID ULLAH: 0009-0008-9756-0667

ABDUS SALAM: 0000-0003-4201-960X

SHINICHI ITSUNO: 0000-0003-0915-3559

DOI

10.55730/1300-0527.3677

Abstract

Cinchona alkaloid-derived sulfonamides and ester dimers containing chiral hyperbranched polymers have been successfully synthesized and applied as catalysts in asymmetric reactions. Several hyperbranched polymers derived from cinchona alkaloids, incorporating sulfonamides and esters, were synthesized through Mizoroki–Heck coupling polymerization. These polymers were subsequently applied in enantioselective Michael addition reactions. As the prepared polymers are not soluble in frequently used organic solvents, they act as efficient catalysts in the enantioselective reaction of β-ketoesters to nitroolefins, achieving up to 99% enantioselectivity with good yields. The insoluble property allows them to better satisfy “green chemistry” requirements and be used several times without losing the enantioselectivity.

Keywords

Hyperbranched polymers, sulfonamide, polymeric chiral organocatalyst, Michael addition reaction

First Page

512

Last Page

523

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

ISLAM, RAFIQUL; ULLAH, MOHAMMAD SHAHID; SALAM, ABDUS; and ITSUNO, SHINICHI (2024) "Preparation of a chiral hyperbranched polymer based on cinchona alkaloids and investigation of its catalytic activity in asymmetric reactions," Turkish Journal of Chemistry: Vol. 48: No. 4, Article 2. https://doi.org/10.55730/1300-0527.3677
Available at: https://journals.tubitak.gov.tr/chem/vol48/iss4/2