Facile addition reactions of allylsilanes to quinolines and isoquinolines activated by chloroformate ester and a catalytic amount of triflate ion

Addition reactions of allylsilanes to quinolines acylated by chloroformate eaters are promoted by a catalytic amount of triflate ion to give 2-allyl-1 ,2-dihydroquinoline derivatives in good yields. A variety of functional gro ups on quinoline ring are tolerated in the reaction. The similar reactions of allylsilanes with isoquinolines afford cyclized benzoisoquinuclidine der ivatives in good yields, along with 1-allyl-1,2-dihydroisoquinoline derivat ives, depending on the reaction conditions. In addition, 2-substituted ally lic silanes can be utilized in the present addition reactions to afford the 2-substituted and 1-substituted 1,2-dihydro-quinolines and -isoquinolines, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.