Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels-Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons

Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeleto...

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Published inAngewandte Chemie International Edition Vol. 51; no. 9; pp. 2084 - 2087
Main Authors Jiang, Xianxing, Shi, Xiaomei, Wang, Shoulei, Sun, Tao, Cao, Yiming, Wang, Rui
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.02.2012
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric synthesis
Aza Compounds - chemical synthesis
Catalysis
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Cyclization
cycloadditions
heterocycles
organocatalysis
Physical Sciences
Science & Technology
Spiro Compounds - chemical synthesis
synthetic methods
organocatalysis
CATALYSIS
KETONES
THIOUREAS
asymmetric synthesis
ACID
ENANTIOSELECTIVE SYNTHESIS
heterocycles
cycloadditions
NITRO-MICHAEL ADDITION
AMINE
synthetic methods
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Summary:Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeletons. The in situ generation of the enolate provides a new way in which to use this important nucleophile in organic synthesis.
Bibliography:istex:71DCDDD27F6234F2AA969E1F6C33EBC9FE9C42BC
ark:/67375/WNG-5VGJ72Z2-R
National Natural Science Foundation of China - No. 20932003; No. 90813012
ArticleID:ANIE201107716
We are grateful for the grants from the National Natural Science Foundation of China (nos. 20932003 and 90813012) and the Key National S&T Program "Major New Drug Development" of the Ministry of Science and Technology of China (2012ZX09504-001-003).
Ministry of Science and Technology of China - No. 2012ZX09504-001-003
We are grateful for the grants from the National Natural Science Foundation of China (nos. 20932003 and 90813012) and the Key National S&T Program “Major New Drug Development” of the Ministry of Science and Technology of China (2012ZX09504‐001‐003).
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201107716