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 inChinese journal of chemistry Vol. 29; no. 5; pp. 973 - 977
Main Author 单凤军 姜岚 李争宁 赵德峰
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.05.2011
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
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
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ISSN1001-604X
1614-7065
DOI10.1002/cjoc.201190198

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Summary: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.
Bibliography: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
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201190198