Methallyl phenyl sulfone

Alternate Names methallyl phenyl sulfone l-(phenylsul-fonyl)-2-methyl-2-propene)... 

Michael Addition. Methallyl phenyl sulfone has been a good partner with a variety of different Michael receptors. Addition to enones using / BuLi as base at —78 °C gave the desired products in good yields. Methyl vinyl ketone afforded the Michael adduct in 61% yield (eq 7). Reaction of methallyl sulfone with 2-hexenone and 2-methyl-2-pentenone in the presence of HMPA provided the conjugate addition products in 91% yield and 79% yield, respectively (eqs 8 and 9).lO.Ha... 

Transition Metal-catalyzed Reactions. Methallyl phenyl sulfone has been a useful allylation reagent for transition metal-catalyzed reactions. Palladium-catalyzed Tsuji-Trost reaction... 

Bromo methallyl sulfone, prepared from methallyl phenyl sulfone, has proven to be a good substrate for stereoselective synthesis of trisubstituted methylenecyclopentanes with a variety of different Michael receptors. For example, the trans trans-trisubstituted methylenecyclopentane was efficiently prepared in 93% yield by a cascade Michael addition/cyclization beginning with ethyl ( )-crotonate (eq 22). The phosphonate sulfone reagent, readily available from methallyl phenyl sulfone, was used for the selective synthesis of 1,3-dienes. The synthesis included... 

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