Journal of Organic Chemistry p. 4424 - 4429 (1984)
Update date:2022-08-04
Topics:
Johnson, Paul R.
White, James D.
The lithium dianions of crotonic and tiglic acids reacted with n-heptanal, benzaldehyde, isobutyraldehyde, 2,2-dimethyl-3,3-dimethoxypropionaldehyde, acetone, and cyclopentanone at -78 deg C, room temperature, and 65 deg C to give α- and γ-condensation products.The kinetically controlled pathway gives largely or entirely the β-hydroxy acid from condensation at the α-carbon, but at higher temperature the reaction is reversible leading to the more stable δ-hydroxy α,β-unsaturated acid.In addition to the reaction temperature, steric effects associated with both the carbonyl electrophile and the acid dianion were found to influence the α:γ ratio of condensation products.
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