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Cyclopropene Derivatives as Precursors to Enantioenriched Cyclopropanols and n ‐Butenals Possessing Quaternary Carbon Stereocenters
Author(s) -
Simaan Marwan,
Delaye PierreOlivier,
Shi Min,
Marek Ilan
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412440
Subject(s) - stereocenter , cyclopropene , chemistry , quaternary carbon , ring (chemistry) , fragmentation (computing) , enantioselective synthesis , stereochemistry , stereoselectivity , carbon fibers , organic chemistry , medicinal chemistry , catalysis , biology , ecology , materials science , composite number , composite material
Abstract The diastereoselective carbocupration reaction of cyclopropenylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo‐ and enantiomerically enriched 2,2,3,3‐tetrasubstituted cyclopropanol derivatives. Ring fragmentation of the copper cyclopropanolate leads to acyclic butenal derivatives possessing enantiomerically enriched α‐quaternary carbon stereocenters in a single‐pot operation.