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Vinylogous Nucleophilic Substitution of the Hydroxy Group in Diarylmethanols with 3‐Propenyl‐2‐silyloxyindoles: Towards the Synthesis of α ‐Alkylidene‐ δ ‐diaryl‐2‐oxindoles
Author(s) -
Jadhav Amol P.,
Ali Amjad,
Singh Ravi P.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601265
Subject(s) - chemistry , stereoselectivity , nucleophilic substitution , selectivity , group (periodic table) , adduct , oxindole , trifluoromethanesulfonate , propenyl , substrate (aquarium) , organic chemistry , stereochemistry , medicinal chemistry , catalysis , oceanography , geology
We report herein a highly stereoselective method for the indium triflate‐catalyzed vinylogous substitution of the hydroxy group of diarylmethyl alcohols with 3‐alkenyl‐2‐silyloxyindoles, which affords broadly substituted α ‐alkylidene‐ δ ‐diaryl‐2‐oxindole products with high efficiency and complete γ ‐site and Z ‐selectivity. The reaction displays very wide substrate scopes for both the reactants, benzhydryl alcohols and 3‐alkenyl‐2‐silyloxyindoles. The utility of the substituted adducts is shown by their conversion to other useful derivatives.