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Tetrahedron
Ravid, U., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
Silverstein, R.M., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
Smith, L.R., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
The highly pure enantiomers of several 4-alkyl (or alkenyl)-γ-lactones of known absolute configuration were synthesized from glutamic acid enantiomers. The key step is selective tosylate displacement rather than ring opening of the lactone tosylate (7→1) by lithium dialkylcuprate or dialkenylcuprate. The enantiomeric purity of synthesized γ-caprolactone was confirmed within the limitations of Pirkle's chiral solvating agent. The enantiomers of synthesized (Z)-6-dodecen-4-olide were used for reference to determine the enantiomeric composition of the pheromone isolated from the black-tailed deer. © 1978.
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Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration
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Ravid, U., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
Silverstein, R.M., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
Smith, L.R., SUNY College of Environmental Science and Forestry, Syracuse, NY, United States
Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration
The highly pure enantiomers of several 4-alkyl (or alkenyl)-γ-lactones of known absolute configuration were synthesized from glutamic acid enantiomers. The key step is selective tosylate displacement rather than ring opening of the lactone tosylate (7→1) by lithium dialkylcuprate or dialkenylcuprate. The enantiomeric purity of synthesized γ-caprolactone was confirmed within the limitations of Pirkle's chiral solvating agent. The enantiomers of synthesized (Z)-6-dodecen-4-olide were used for reference to determine the enantiomeric composition of the pheromone isolated from the black-tailed deer. © 1978.
Scientific Publication
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