Base-enabled access to diastereoselective spirofuran oxindoles and γ-functionalized allenoates

Base-enabled access to diastereoselective spirofuran oxindoles and γ-functionalized allenoates

Base assisted divergent reactivity of isatins and allenoates has been achieved, which afforded diastereoselective spirofuran oxindoles and γ-functionalized allenoates. The DBU mediated Morita-Baylis-Hillman (MBH) reaction followed by the cascade annulation through the stabilized β-ammonium enolate i...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2021-02, Vol.57 (14), p.1746-1749
Hauptverfasser: , Krishnan, Jagadeesh, Suresh, Eringathodi, Somappa, Sasidhar B
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Sprache:eng
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Chemical reactions
Crystallography
NMR
Nuclear magnetic resonance
Stereoselectivity
Substrates
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Krishnan, Jagadeesh


Suresh, Eringathodi
Somappa, Sasidhar B
description Base assisted divergent reactivity of isatins and allenoates has been achieved, which afforded diastereoselective spirofuran oxindoles and γ-functionalized allenoates. The DBU mediated Morita-Baylis-Hillman (MBH) reaction followed by the cascade annulation through the stabilized β-ammonium enolate intermediate led to the spiro-framework, wherein DABCO furnished the γ-functionalized allenoates. The protocol offers access to biologically relevant functionalized oxindole scaffolds with an excellent substrate scope under mild reaction conditions. Base assisted divergent reactivity of isatins and allenoates has been achieved, which afforded diastereoselective spirofuran oxindoles and γ-functionalized allenoates.
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Chemical reactions
Crystallography
NMR
Nuclear magnetic resonance
Stereoselectivity
Substrates
title Base-enabled access to diastereoselective spirofuran oxindoles and γ-functionalized allenoates
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