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Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates
Author(s) -
Vertesaljai Peter,
Navaratne Primali V.,
Grenning Alexander J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508100
Subject(s) - knoevenagel condensation , trimethylenemethane , chemistry , alkylation , adduct , palladium , deprotonation , allylic rearrangement , medicinal chemistry , organic chemistry , catalysis , cycloaddition , ion
Abstract Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3‐difunctionalization through a sequence of selective γ‐deprotonation/α‐alkylation and palladium(0)‐catalyzed allylic alkylation. Herein, we report the discovery and development of a three‐component 1,3‐difunctionalization of Knoevenagel adducts as well as a unique palladium(0)‐catalyzed branch‐selective allylic alkylation.