The First Catalytic Asymmetric Morita-Baylis-Hillman Reaction of Acrolein with Aromatic Aldehydes

We report the first example of catalytic asymmetric Morita-Baylis-Hillman reaction of acrolein with aromatic aldehydes. The use of 10 mol% of Hatakeyama＇s catalyst β-isocupreidine C4, in combination with 20 mol% of 2,6-dimethoxybenzoic acid, could catalyze the reaction to give the desired products i...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 30; no. 11; pp. 2631 - 2635
Main Author 曾兴平 刘运林 计从斌 周剑
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.11.2012
WILEY‐VCH Verlag
Wiley
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Subjects
2,6‐dimethoxybenzoic acid
6-dimethoxybenzoic acid
acrolein
Aldehydes
Baylis-Hillman反应
Chemistry
Chemistry, Multidisciplinary
Morita-Baylis-Hillman reaction
organocatalysis
Physical Sciences
Science & Technology
β-isocupreidine
不对称催化
丙烯醛
二甲氧基苯甲酸
催化剂
摩尔
芳香醛
2,6-dimethoxybenzoic acid
organocatalysis
PRESSURE
ORGANOCATALYSTS
ENANTIOSELECTIVE SYNTHESIS
N-SULFONATED IMINES
HILIMAN REACTION
ALLYLATION
Morita-Baylis-Hillman reaction
beta-isocupreidine
acrolein
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Summary:We report the first example of catalytic asymmetric Morita-Baylis-Hillman reaction of acrolein with aromatic aldehydes. The use of 10 mol% of Hatakeyama＇s catalyst β-isocupreidine C4, in combination with 20 mol% of 2,6-dimethoxybenzoic acid, could catalyze the reaction to give the desired products in up to 81% ee.
Bibliography:31-1547/O6
Morita-Baylis-Hillman reaction, acrolein,β-isocupreidine, 2,6-dimethoxybenzoic acid, organocatalysis
We report the first example of catalytic asymmetric Morita-Baylis-Hillman reaction of acrolein with aromatic aldehydes. The use of 10 mol% of Hatakeyama＇s catalyst β-isocupreidine C4, in combination with 20 mol% of 2,6-dimethoxybenzoic acid, could catalyze the reaction to give the desired products in up to 81% ee.
Zeng, Xingping Liu, Yunlin Ji, Congbina Zhou, Jian＊＇a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China
ArticleID:CJOC201200937
Specialized Research Fund for the Doctoral Program of Higher Education - No. 20090076120007
istex:05A618CE42DE93E7874EF33CD88A267222C9F15C
Innovation Program of SMEC - No. 12ZZ046
NSFC - No. 20902025
the Fundamental Research Funds for the Central Universities - No. East China Normal University 11043
the 973 program - No. 2011CB808600
ark:/67375/WNG-2NVTFGTG-G
ObjectType-Article-1
SourceType-Scholarly Journals-1
content type line 14
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201200937