Synthesis of 1,3-cyclohexadienes by tandem diene-alkyne metathesis: improved procedure |
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Authors: | Mark D. Middleton |
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Affiliation: | Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA |
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Abstract: | A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxylation (Bäckvall reaction) for cyclohexadiene functionalization. |
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Keywords: | Enyne metathesis Cross metathesis 1,3-Cyclohexadienes Tetrahydroquinoline Grubbs catalyst Hoveyda catalyst |
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