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Synthesis of Highly Functionalized Aminoindolizines by Titanium(IV) Chloride Mediated Cycloisomerization and Phosphine‐Catalyzed Aza‐Michael Addition Reactions
Author(s) -
Wang De,
Wei Yin,
Shi Min
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300062
Subject(s) - cycloisomerization , chemistry , michael reaction , phosphine , catalysis , organic chemistry , combinatorial chemistry , titanium
TiCl‐ing your fancy : A simple and highly efficient synthetic method for the preparation of indolizines from the reaction of 2‐enoylpyridines with sulfonamides in the presence of TiCl 4 under mild conditions has been developed. A subsequent phosphine‐catalyzed aza‐Michael reaction of the corresponding indolizines with vinyl ketones and activated allenes was also developed, which affords highly functionalized indolizines in excellent yields under mild conditions.