ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst
Under the acyclic diene metathesis (ADMET) reaction condition, the C3-vinyl groups of cinchona alkaloids readily react with each other to form a C-C bond. A novel type of cinchona alkaloid polymers was synthesized from dimeric cinchona squaramides using the Hoveyda-Grubbs’ second-generation catalyst...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-05-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/10/5/591 |
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| author | Mohammad Shahid Ullah Sadia Afrin Chhanda Shinichi Itsuno |
| author_facet | Mohammad Shahid Ullah Sadia Afrin Chhanda Shinichi Itsuno |
| author_sort | Mohammad Shahid Ullah |
| collection | DOAJ |
| description | Under the acyclic diene metathesis (ADMET) reaction condition, the C3-vinyl groups of cinchona alkaloids readily react with each other to form a C-C bond. A novel type of cinchona alkaloid polymers was synthesized from dimeric cinchona squaramides using the Hoveyda-Grubbs’ second-generation catalysts (<b>HG<sub>2</sub></b>) by means of ADMET reaction. The chiral polymers, containing cinchona squaramide moieties in their main chains, were subsequently employed as catalysts for the enantioselective Michael reaction to give the corresponding chiral adducts in high yields with excellent enantioselectivity and diastereoselectivity. Both enantiomers from the asymmetric Michael reaction were distinctively prepared while using the polymeric catalysts, possessing pseudoenantiomeric structures. The catalysts were readily recovered from the reaction mixture and recycled several times due to the insolubility of the cinchona-based squaramide polymers. |
| first_indexed | 2024-03-10T19:36:21Z |
| format | Article |
| id | doaj.art-277c9d8b51a74ba780b9ca4f09f0cdee |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T19:36:21Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-277c9d8b51a74ba780b9ca4f09f0cdee2023-11-20T01:37:09ZengMDPI AGCatalysts2073-43442020-05-0110559110.3390/catal10050591ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric OrganocatalystMohammad Shahid Ullah0Sadia Afrin Chhanda1Shinichi Itsuno2Department of Applied Chemistry and Life Science, Toyohashi University of Technology, Toyohashi 441-8580, JapanDepartment of Applied Chemistry and Life Science, Toyohashi University of Technology, Toyohashi 441-8580, JapanDepartment of Applied Chemistry and Life Science, Toyohashi University of Technology, Toyohashi 441-8580, JapanUnder the acyclic diene metathesis (ADMET) reaction condition, the C3-vinyl groups of cinchona alkaloids readily react with each other to form a C-C bond. A novel type of cinchona alkaloid polymers was synthesized from dimeric cinchona squaramides using the Hoveyda-Grubbs’ second-generation catalysts (<b>HG<sub>2</sub></b>) by means of ADMET reaction. The chiral polymers, containing cinchona squaramide moieties in their main chains, were subsequently employed as catalysts for the enantioselective Michael reaction to give the corresponding chiral adducts in high yields with excellent enantioselectivity and diastereoselectivity. Both enantiomers from the asymmetric Michael reaction were distinctively prepared while using the polymeric catalysts, possessing pseudoenantiomeric structures. The catalysts were readily recovered from the reaction mixture and recycled several times due to the insolubility of the cinchona-based squaramide polymers.https://www.mdpi.com/2073-4344/10/5/591ADMETcinchona alkaloidsquaramidepolymeric organocatalystMichael additionpseudoenantiomer |
| spellingShingle | Mohammad Shahid Ullah Sadia Afrin Chhanda Shinichi Itsuno ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst Catalysts ADMET cinchona alkaloid squaramide polymeric organocatalyst Michael addition pseudoenantiomer |
| title | ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst |
| title_full | ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst |
| title_fullStr | ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst |
| title_full_unstemmed | ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst |
| title_short | ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst |
| title_sort | admet polymerization of dimeric cinchona squaramides for the preparation of a highly enantioselective polymeric organocatalyst |
| topic | ADMET cinchona alkaloid squaramide polymeric organocatalyst Michael addition pseudoenantiomer |
| url | https://www.mdpi.com/2073-4344/10/5/591 |
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