ビニル,アリルスルホンの立体選択的合成と"Syn効果"
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概要
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Regio- and stereoselective synthesis of (<I>E</I>) - and (<I>Z</I>) -vinyl sulfones, which made it feasible to investigate the stereochemistry of the conversion of vinyl sulfones to the corresponding allyl sulfones under basic conditions, was accomplished <I>via</I> iodosulfonization of 1-alkenes or 1-alkynes. It was found that (<I>E</I>) -vinyl sulfones preferentially afforded (Z) -allyl sulfones as kinetically-controlled products, while (<I>Z</I>) - and α-substituted vinyl sulfones gave (<I>E</I>) -allyl sulfones. Such stereochemical relationship was rationalized by "<I>syn</I>-effect, " and its relative degree for various substituents was determined by observation of <I>E</I>/<I>Z</I> ratios of the allyl sulfones resulted from the corresponding γ-mono- and disubstituted vinyl sulfones. X-ray crystallography was performed for some vinyl sulfones and the related compounds to reveal the origin of "<I>syn</I>-effect." On the other hand, the convenient new methods for the preparation of allyl sulfones and desulfonylation of their alkylated derivatives were successfully employed for the syntheses of squalene, (±) -recifeiolide, coenzyme Q<SUB>10</SUB>, (±) -lavandulol, and isolavandulol.
- 有機合成化学協会の論文