Asymmetric Conjugate Addition to Cyclic Enone Catalyzed by Cu-NHC Complexes with C2 Symmetry
A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of...
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| Published in | Chinese journal of chemistry Vol. 29; no. 5; pp. 973 - 977 |
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| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.05.2011
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| ISSN | 1001-604X 1614-7065 |
| DOI | 10.1002/cjoc.201190198 |
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| Abstract | A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiorner was observed when different bases or copper sources were utilized. |
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| AbstractList | A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiorner was observed when different bases or copper sources were utilized. A series of chiral, C2 symmetric tridentate N‐heterocyclic carbene precursors, containing two N‐functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex‐2‐enone and cyclopent‐2‐enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiomer was observed when different bases or copper sources were utilized. C2 symmetric, tridentate N‐heterocyclic carbene precursors, containing two N‐functionalized hydroxyl or alkoxyl groups, were synthesized and applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex‐2‐enone and cyclopent‐2‐ enone with up to 76% ee, and 65% ee, respectively. Flip of major enantiomer was observed when different bases or copper sources were utilized. A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiomer was observed when different bases or copper sources were utilized. |
| Author | Jiang, Lan Li, Zhengning Zhao, Defeng Shan, Fengjun |
| AuthorAffiliation | College of Environmental and Chemical Engineering, Dalian University, Dalian, Liaoning 116622, China Liaoning Key Laboratory of Bioorganic Chemistry, Dalian University, Dalian, Liaoning 116622, China State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116012, China |
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| Copyright | Copyright © 2011 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2011 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Notes | 31-1547/O6 A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiorner was observed when different bases or copper sources were utilized. Shan Fengjuna, Jiang Lan,Li Zhengning, Zhao Defeng（ a College of Environmental and Chemical Engineering, Dalian University, Dalian, Liaoning 116622, China b Liaoning Key Laboratory of Bioorganic Chemistry, Dalian University, Dalian, Liaoning 116622, China c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116012, China） asymmetric catalysis, copper-NHC, irnidazolinium salt, C2 symmetry, Michael addition istex:40259878E612D15C0E08A9D7B4800CD28DD7EE11 ark:/67375/WNG-G226PR3V-Q the National Natural Science Foundation of China - No. 20672016, 2097202 ArticleID:CJOC201190198 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
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| SubjectTerms | asymmetric catalysis C2 symmetry C2对称性 copper-NHC imidazolinium salt Michael addition 不对称 催化 共轭加成 循环 杂环卡宾 环戊二烯酮 铜配合物 |
| Title | Asymmetric Conjugate Addition to Cyclic Enone Catalyzed by Cu-NHC Complexes with C2 Symmetry |
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