ol8b01082_si_001.pdf (3.01 MB)
Stereoselective Synthesis of Medium-Sized Cyclic Ethers by Sequential Ring-Closing Metathesis and Tsuji–Trost Allylation
journal contribution
posted on 2018-04-20, 17:21 authored by James Skardon-Duncan, Michael Sparenberg, Alexandre Bayle, Sam Alexander, J. Stephen ClarkFully functionalized
medium-sized cyclic ethers, of the type found
in fused polyether natural products, have been prepared by sequential
ring-closing diene metathesis, conversion of the resulting cyclic
enone into an allylic enol carbonate, and Tsuji–Trost allylation
using a chiral palladium complex. Very high levels of diastereocontrol,
favoring the diastereomer in which there is a cis relationship between the allyl group at C-2 of the medium-ring ether
and the substituent at C-7/C-8, are obtained in cases where catalyst
control and substrate control are matched.
History
Usage metrics
Categories
Keywords
cyclic etherscis relationshipfunctionalizedTsujisequential ring-closing diene metathesisStereoselective Synthesischiral palladiumconversionSequential Ring-Closing MetathesisMedium-Sized Cyclic Ethersallylic enol carbonatemedium-ring etherAllylationcatalyst controltypepolyethersubstituentdiastereomerallylationallyl groupsubstrate controldiastereocontrolC -2cyclic enone
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC