Enantioselective synthesis of substituted indanones from silyloxyallenes.
A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl(2)(PPh(3))(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.
Brekan
Jonathan A
JA
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, USA.
Reynolds
Troy E
TE
Scheidt
Karl A
KA
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D007189:Indans; D007192:Indenes; D017646:Organosilicon Compounds