STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-TRANS-SPIRO-BETA-LACTONES BY DIELS-ALDER CYCLOADDITION OF 1,3-DIENES TO ALPHA-METHYLENE-BETA-LACTONE AND THEIR DECARBOXYLATION BY PYROLYSIS TO (E)-ALKYLIDENECYCLOALKENES, A CONVENIENT OLEFINATION METHOD
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ADAM, W
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MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANYMAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
ADAM, W
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SALGADO, VON
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MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANYMAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
SALGADO, VON
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PETERS, EM
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MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANYMAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
PETERS, EM
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PETERS, K
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MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANYMAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
PETERS, K
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VONSCHNERING, HG
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MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANYMAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
VONSCHNERING, HG
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[1] MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY
A number of spiro-beta-lactones was prepared in good to excellent yields through stereoselective [4 + 2] cycloaddition of beta-isopropyl-alpha-methylene-beta-lactone (1) with acyclic, cyclic, heterocyclic and aromatic 1,3-dienes by sealed-tube reaction at moderate temperatures (50 - 130-degrees-C). Flash pyrolysis of the resulting spiro-beta-lactones 2 in the gas phase at 400-degrees-C afforded by decarboxylation exclusively the corresponding (E)-isopropylidenealkenes in high yields with retention of the initial geometry and without double bond isomerization. This olefination method constitutes an excellent stereoselective synthesis of (E)-alkylidenecycloalkenes.