ChemInform Abstract: Reaction of the Lithium Derivative of Diethyl 2-(or 3-) Methylphenylmethanephosphonate with Ketones. An Example of High Syn- Stereoselectivity.
Abstract
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ChemInform Abstract
The reaction of the Li derivatives of the arylmethanephosphonates (I) with a large number of sym. and unsym. ketones, e.g. (II) and (V), is studied. The corresponding adducts such as (III) and diastereomeric mixtures (VI) and (VII) with prevailing “threo” isomer are isolated. The results of stereospecific olefination of some β- hydroxyphosphonates, e.g. (IIIc) → (IV), indicate the influence of combined steric effects in ketones and ortho- and meta-substituted benzylphosphonates (I). Spectral investigations and PM3-calculations prove high synstereoselectivity of the reaction of ortho-methyl- substituted benzylphosphonates with the studied ketones.
