jo302460d_si_002.cif (143.19 kB)
Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ‑Substituted Allenoates: Systematic Studies and Targeted Applications
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posted on 2013-02-15, 00:00 authored by Catherine Gomez, Maxime Gicquel, Jean-Christophe Carry, Laurent Schio, Pascal Retailleau, Arnaud Voituriez, Angela MarinettiThe phosphine-promoted [3 + 2] cyclizations between γ-substituted
allenoates and arylideneoxindoles have been applied to the stereoselective
synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene
units. It has been demonstrated that PPh3 operates a very
efficient control of the relative stereochemistry of the three stereogenic
centers of the final spiranic products. Focused experiments have been
carried out then so as to access carbocyclic analogues of an important
series of anticancer agents inhibiting MDM2-p53 interactions.
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Allenoatestereoselective synthesisspiranic productsFocused experimentsallenoatespiroMDMTargetedcyclizationaccess carbocyclic analoguesarylideneoxindoleSystematic Studiesseriestrisubstituted cyclopentene unitsstereochemistrySynthesiSubstitutedanticancer agentsstereogenic centersApplicationsTheSpirocyclopenteneoxindoleinteractionPPh 3
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