Premium
A New Golden Age for Donor–Acceptor Cyclopropanes
Author(s) -
Schneider Tobias F.,
Kaschel Johannes,
Werz Daniel B.
Publication year - 2014
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.201309886
Subject(s) - cyclopropane , ring (chemistry) , vicinal , chemistry , acceptor , ring strain , electron donor , electron acceptor , stereochemistry , combinatorial chemistry , computational chemistry , photochemistry , organic chemistry , catalysis , physics , condensed matter physics
The effective use of ring strain has been applied to considerable advantage for the construction of complex systems. The focus here is directed towards cyclopropanes as building blocks for organic synthesis. Although thermodynamics should take the side of synthetic chemists, only a specific substitution pattern at the cyclopropane ring allows for particularly mild, efficient, and selective transformations. The required decrease in the activation barrier is achieved by the combined effects of vicinal electron‐donating and electron‐accepting moieties. This Review highlights the appropriate tools for successfully employing donor–acceptor cyclopropanes in ring‐opening reactions, cycloadditions, and rearrangements.