Stereoselective Synthesis of Medium-Sized Cyclic Ethers
by Sequential Ring-Closing Metathesis and Tsuji–Trost Allylation
Version 2 2018-05-14, 23:43
Version 1 2018-04-20, 17:21
Posted on 2018-05-14 - 23:43
Fully 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.
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Skardon-Duncan, James; Sparenberg, Michael; Bayle, Alexandre; Alexander, Sam; Clark, J. Stephen (2018). Stereoselective Synthesis of Medium-Sized Cyclic Ethers
by Sequential Ring-Closing Metathesis and Tsuji–Trost Allylation. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b01082
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AUTHORS (5)
JS
James Skardon-Duncan
MS
Michael Sparenberg
AB
Alexandre Bayle
SA
Sam Alexander
JC
J. Stephen Clark
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