Premium
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 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.201412440
Subject(s) - stereocenter , cyclopropene , quaternary carbon , chemistry , fragmentation (computing) , ring (chemistry) , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , biology , ecology
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.