✍ Scribed by Alain Krief; François Couty
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Benzylselenidesbearing a y-alkenyk-sulfonyloxyside chain react with butyllithiums to produce, viatha corresponding benzyllithiums, l-aryl-2-vinyl cyclopropanes. @ 1997Published by ElsevierScience Ltd. Some time ago, we diaclosed that benzyllithiumshave an exceptional propensityto add to inactivated C,C double bond especially if it ia built in the molecule.' This reaction allowed the synthesis of l-aryl-2-Iithiomethylcyclopentanes and cyclohexanes in high yield and with almost complete stereocontroi (Scheme 1)."2 It nevertheless could not be extended to the synthesis of related three or four membered cycles probably due to the strain involved. It is in fact known that the reaction works in the other direction and that Iithiomethylcyclopropanesundergo ring fragmentationleading to the correspondingyalkenyllithiums.3 Scheme 1 Ph
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