Abstract

The reaction of phenylpropargyl aldehyde diethyl acetal with 1-phenyl-3,4-dimethylphosphole at 140°C or 1,2,5-triphenylphosphole at 170°C leads, after deprotection, to the corresponding 1-phosphanorbornadiene-2-carboxaldehydes 3 and 4 in 88 and 45% yields, respectively. The resolution of 3 and 4 was carried out by chromatography or fractional crystallization of the acetals derived from ( S,S)-1,2-diphenylethane-1,2-diol. The absolute configurations were established by X-ray analysis of one of these acetals or of a 2-bromomethyl derivative.

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