01587nas a2200193 4500008004100000245009400041210006900135260000800204300001600212490000700228520085000235653007801085100002301163700001401186700002601200700002401226700002201250856012101272 2016 eng d00aLewis acid catalyzed selective reactions of donor-acceptor cyclopropanes with 2-naphthols0 aLewis acid catalyzed selective reactions of donoracceptor cyclop cAUG a10061-100640 v553 a

Lewis acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with 2-naphthols is reported. The reaction exhibits tunable selectivity depending on the nature of Lewis acid employed and proceed as a dearomatization/rearomatization sequence. With Bi(OTf)(3) as the Lewis acid, a highly selective dehydrative [3+2] cyclopentannulation takes place leading to the formation of naphthalene-fused cyclopentanes. Interestingly, engaging Sc(OTf)(3) as the Lewis acid, a Friedel-Crafts-type addition of 2-naphthols to cyclo-propanes takes place, thus affording functionalized 2-naphthols. Both reactions furnished the target products in high regioselectivity and moderate to high yields.

10aannulations; arenes; Lewis acids; reaction mechanisms; small ring systems1 aKaicharla, Trinadh1 aRoy, Tony1 aThangaraj, Manikandan1 aGonnade, Rajesh, G.1 aBiju, Akkattu, T. uhttps://library.ncl.res.in/content/lewis-acid-catalyzed-selective-reactions-donor-acceptor-cyclopropanes-2-naphthols