Bicyclic Guanidine-Catalyzed Direct Asymmetric Allylic Addition of N-Aryl Alkylidene-Succinimides

Enantio‐enriched maleimides and succinimides that can be used to prepare aza‐heterocycles with multiple chiral centers are obtained from the bicyclic guanidine‐catalyzed direct asymmetric allylic addition of N‐aryl alkylidene‐succinimides to imines. NMR studies and deuterium‐exchange experiments wer...

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Published inChemistry : a European journal Vol. 16; no. 42; pp. 12534 - 12537
Main Authors Wang, Jianmin, Liu, Hongjun, Fan, Yitian, Yang, Yuanyong, Jiang, Zhiyong, Tan, Choon-Hong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.11.2010
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
allylation
asymmetric synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Combinatorial Chemistry Techniques
guanidine
Guanidine - chemistry
Magnetic Resonance Spectroscopy
Maleimides - chemical synthesis
Maleimides - chemistry
Mannich reactions
Physical Sciences
Science & Technology
Stereoisomerism
Succinimides - chemical synthesis
Succinimides - chemistry
ENANTIOSELECTIVE PROTONATION
HYDROGENATION
ALLYLBORATION
ISOMERIZATION
COMPLEXES
Mannich reactions
BASE
guanidine
KETONES
asymmetric synthesis
CROTYLATION
allylation
DERIVATIVES
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Summary:Enantio‐enriched maleimides and succinimides that can be used to prepare aza‐heterocycles with multiple chiral centers are obtained from the bicyclic guanidine‐catalyzed direct asymmetric allylic addition of N‐aryl alkylidene‐succinimides to imines. NMR studies and deuterium‐exchange experiments were used to study the intermediates in the reaction.
Bibliography:istex:1A9A5F87F7975DA8CDBF8BF0C37483CE9DCB69D7
ARF - No. R-143-000-376-112; No. R-143-00-346-113; No. R-143-000-337-112
ark:/67375/WNG-JLX207L2-Q
ArticleID:CHEM201002183
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201002183