TY - JOUR AU - Grandclaudon, Charlotte; Ruamps, Mirko; Duboc, Raphaël; Michelet, Véronique; Toullec, Patrick Y. TI - Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions SN - 0936-5214 SN - 1437-2096 PY - 2018 JO - Synlett JF - Synlett LA - EN VL - 29 IS - 09 SP - 1181 EP - 1186 ET - 2018/04/09 DA - 2018/05/18 KW - organocatalysis KW - Lewis base KW - halogenation KW - carbocyclization KW - enynes AB - Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosuccinimides with up to a 30-fold increase of the initial reaction rate with respect to the background reaction. Phosphorus sulfides and selenides showed the best catalytic activity for the iodocarbocyclization of a cinnamylaniline derivative in the presence of diiodohydantoin. An asymmetric variant of the iodocarbocyclization reaction of an alkynylstyrene using a chiral phosphorus selenide resulted in a modest enantioselectivity. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1591982 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1591982 ER -