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Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition
Author(s) -
Sabbatani Juliette,
Maulide Nuno
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.201601340
Subject(s) - oxocarbenium , cycloaddition , cyclopropane , chemistry , malonate , ion , photochemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , nucleophile , ring (chemistry)
A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.