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Efficient Entry to Tetrahydropyridines: Addition of Enol Ethers to Allenesulfonamides Involving a Novel 1,3-Sulfonyl Shift
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1999
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Chemical EngineeringEngineeringEnol EthersOrganic ChemistryCatalysisAllenesulfonamides InvolvingChemistrySynthetic ChemistryTetrahydropyridine DerivativesEfficient EntryStereoselective SynthesisNovel 1,3-Sulfonyl ShiftEnantioselective Synthesis
Heating at 70–100°C is all that is needed to induce a novel 1,3-sulfonyl shift in the reaction of N-allenesulfonamides with enol ethers [Eq. (a)]. Tetrahydropyridine derivatives are obtained in excellent yields and with high stereoselectivities.