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Chiral Induction in [2+2+2] Cycloaddition Reactions
Author(s) -
PlaQuintana Anna,
Roglans Anna
Publication year - 2018
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.201800291
Subject(s) - cycloaddition , chirality (physics) , chemistry , asymmetric induction , enantioselective synthesis , axial chirality , computational chemistry , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , physics , symmetry breaking , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model
Chiral compounds containing six‐membered rings, whether aromatic or not, are of interest in a wide range of disciplines, including material science, medicinal chemistry, and agrochemistry. As transition‐metal‐catalyzed [2+2+2] cycloaddition reactions are one of the most elegant routes for the construction of six‐membered rings, significant effort has been given to developing asymmetric variants. In this focus review, we bring together the work that has been done in optimizing diastereoselective [2+2+2] cycloaddition reactions of enantiomerically pure substrates. Two different approaches—chirality induction and chirality transfer—are considered in a review organized by the type of chiral element being constructed (central, axial, or helical). The general challenges that are involved are highlighted and possible future directions in the field are discussed.