Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives
A number of upper rim-functionalized calix[4]thiourea cyclohexanediamine derivatives have been designed, synthesized and used as catalysts for enantioselective Michael addition reactions between nitroolefins and acetylacetone. The optimal catalyst 2 with a mono-thiourea group exhibited good performa...
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Beilstein-Institut
2018-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.164 |
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doaj-2c0ac4d6398d439e8bbdbe929fe853a82021-04-02T06:59:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-07-011411901190710.3762/bjoc.14.1641860-5397-14-164Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivativesZheng-Yi Li0Hong-Xiao Tong1Yuan Chen2Hong-Kui Su3Tangxin Xiao4Xiao-Qiang Sun5Leyong Wang6Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaJiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, ChinaA number of upper rim-functionalized calix[4]thiourea cyclohexanediamine derivatives have been designed, synthesized and used as catalysts for enantioselective Michael addition reactions between nitroolefins and acetylacetone. The optimal catalyst 2 with a mono-thiourea group exhibited good performance in the presence of water/toluene (v/v = 1:2). Under the optimal reaction conditions, high yields of up to 99% and moderate to good enantioselectivities up to 94% ee were achieved. Detailed experiments clearly showed that the upper rim-functionalized hydrophobic calixarene scaffold played an important role in cooperation with the catalytic center to the good reactivities and enantioselectivities.https://doi.org/10.3762/bjoc.14.164asymmetric Michael addition reactioncalix[4]arenecyclohexanediaminethiourea |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Zheng-Yi Li Hong-Xiao Tong Yuan Chen Hong-Kui Su Tangxin Xiao Xiao-Qiang Sun Leyong Wang |
| spellingShingle |
Zheng-Yi Li Hong-Xiao Tong Yuan Chen Hong-Kui Su Tangxin Xiao Xiao-Qiang Sun Leyong Wang Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives Beilstein Journal of Organic Chemistry asymmetric Michael addition reaction calix[4]arene cyclohexanediamine thiourea |
| author_facet |
Zheng-Yi Li Hong-Xiao Tong Yuan Chen Hong-Kui Su Tangxin Xiao Xiao-Qiang Sun Leyong Wang |
| author_sort |
Zheng-Yi Li |
| title |
Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| title_short |
Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| title_full |
Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| title_fullStr |
Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| title_full_unstemmed |
Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| title_sort |
asymmetric michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2018-07-01 |
| description |
A number of upper rim-functionalized calix[4]thiourea cyclohexanediamine derivatives have been designed, synthesized and used as catalysts for enantioselective Michael addition reactions between nitroolefins and acetylacetone. The optimal catalyst 2 with a mono-thiourea group exhibited good performance in the presence of water/toluene (v/v = 1:2). Under the optimal reaction conditions, high yields of up to 99% and moderate to good enantioselectivities up to 94% ee were achieved. Detailed experiments clearly showed that the upper rim-functionalized hydrophobic calixarene scaffold played an important role in cooperation with the catalytic center to the good reactivities and enantioselectivities. |
| topic |
asymmetric Michael addition reaction calix[4]arene cyclohexanediamine thiourea |
| url |
https://doi.org/10.3762/bjoc.14.164 |
| work_keys_str_mv |
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