6533b831fe1ef96bd1298715

RESEARCH PRODUCT

Combining organocatalysis and lanthanide catalysis: a sequential one-pot quadruple reaction sequence/hetero-Diels-Alder asymmetric synthesis of functionalized tricycles

Dieter EndersSimon DochainRakesh PuttreddyKari RissanenFabrizio Vetica

subject

LanthanideheterocyclesChemistry010405 organic chemistryasymmetric catalysis; heterocycles; lanthanides; organocatalysis; synthetic methodsEnantioselective synthesisasymmetric catalysisSequence (biology)General ChemistryGeneral Medicine010402 general chemistry01 natural sciencesCatalysisCatalysis0104 chemical sciencesOrganocatalysisDiels aldersynthetic methodsOrganic chemistryAmine gas treatingStereoselectivitylanthanidesorganocatalysista116

description

A stereoselective one-pot synthesis of functionalized complex tricyclic polyethers has been achieved using the combination of secondary amine and lanthanide catalysis. This one-pot quadruple reaction/Hetero-Diels–Alder sequence gave good yields (per step) as well as excellent diastereo- and enantioselectivities. Furthermore, the particular combination of lanthanide complexes with organocatalysis is one of the first examples described for sequential catalysis.

10.1002/anie.201610196http://hdl.handle.net/11573/1438016