Tetrahedron p. 749 - 756 (1984)
Update date:2022-08-05
Topics:
Maio, G. Di
Vecchi, E.
Zeuli, E.
Delfini, M
Alkylation of methyl 4-methyl 5-oxo 5-phenyl (m and p-X substituted) pentanoates 1a-h give cis and trans tetrahydro 5,6-dimethyl 6-phenyl 2H pyran-2-ones.LFER of isomer ratios as function of the X substituent on the phenyl ring is seen in MeLi-Et2O.The lactone ratios of the reactions in THF with MeMgCl are not affected by the X phenyl substituent, while a more complex situation is showed by reactions of MeMgCl in Et2O and benzene.Changes in the cis: trans-ratios with variations in reactant and solvent are discussed in terms of equilibrium between folded and unfolded conformations in transition states.
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