Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles

The first highly enantioselective formal [4+2] tandem cyclizations between isatylidenemalononitriles and activated dienes catalyzed by bifunctional chiral phosphine catalysts have been developed, yielding multistereogenic spirocyclic oxindoles in high yields and excellent optical purity. This reacti...

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Published inAdvanced synthesis & catalysis Vol. 356; no. 4; pp. 736 - 742
Main Authors Hu, Fang-Le, Wei, Yin, Shi, Min
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 10.03.2014
WILEY‐VCH Verlag
Wiley
Subjects
Activated
activated dienes
asymmetric [4+2] cyclization
Asymmetry
Catalysis
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
chiral phosphines
Dienes
multistereogenic spirocyclic oxindoles
organocascade reactions
Phosphines
Physical Sciences
Purity
Science & Technology
Synthesis
FACILE CREATION
ACID
chiral phosphines
asymmetric [4+2]cyclization
N-SULFONATED IMINES
BAYLIS-HILLMAN REACTION
multistereogenic spirocyclic oxindoles
FUNCTIONALIZED CYCLOPENTENES
activated dienes
SPIROOXINDOLES
organocascade reactions
3+2 ANNULATION
CYCLOADDITION
ISATINS
CONSTRUCTION
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Summary:The first highly enantioselective formal [4+2] tandem cyclizations between isatylidenemalononitriles and activated dienes catalyzed by bifunctional chiral phosphine catalysts have been developed, yielding multistereogenic spirocyclic oxindoles in high yields and excellent optical purity. This reaction is accomplished via a tandem Rauhut–Currier/Michael/Rauhut–Currier reaction sequence.
Bibliography:Fundamental Research Funds for the Central Universities
ark:/67375/WNG-BWN3M999-S
National Natural Science Foundation of China - No. 21072206, 20472096, 21102166, 21372241, 21302203, 20672127, 21121062 and 20732008
National Basic Research Program of China - No. (973)-2010CB833302
istex:0221C499A32489C4ADA8E5C6DFCCB2C1A9BE93FD
ArticleID:ADSC201301070
Shanghai Municipal Committee of Science and Technology - No. 11JC1402600
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201301070