Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters

A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with exc...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 52; no. 36; pp. 6162 - 6165
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Adducts
Asymmetry
Cascades
catalytic activity
chemical compounds
chemical reactions
Chemistry
Chemistry, Multidisciplinary
Construction
Michael reaction
Physical Sciences
Science & Technology
Stereoselectivity
Synthesis (chemistry)
Transformations
OXINDOLES
DOMINO REACTIONS
ACID
ALPHA-ALKYLIDENE SUCCINIMIDES
ENANTIOSELECTIVE CONSTRUCTION
1,3-DIPOLAR CYCLOADDITION
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Summary:A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct. Squaramide-catalyzed cascade Michael/Michael reaction for the asymmetric synthesis of five-membered spirooxindoles containing five contiguous stereocenters is presented.
Bibliography:1
For ESI and crystallographic data in CIF or other electronic format see DOI
13
Electronic supplementary information (ESI) available: Experimental procedure, copies of
H and
10.1039/c6cc00705h
1446037
C NMR spectra of new compounds, and HPLC chromatograms. CCDC
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c6cc00705h