TY - JOUR AU - Beckendorf, Stephan; Mancheño, Olga García TI - 'Click'-BINOLs: A New Class of Tunable Ligands for Asymmetric Catalysis SN - 0039-7881 SN - 1437-210X PY - 2012 JO - Synthesis JF - Synthesis LA - EN VL - 44 IS - 14 SP - 2162 EP - 2172 ET - 2012/05/25 DA - 2012/07/06 KW - Lewis acids KW - asymmetric catalysis KW - 'click' chemistry KW - BINOL ligands KW - alkynes KW - aldehydes KW - diethylzinc additions AB - A new class of easily tunable 1,2,3-triazole-BINOL ligands, 'click'-BINOLs, have been synthesized from readily available alkynes and several azido-BINOL derivatives using the powerful Huisgen [3+2] cycloaddition 'click' approach. The activity of these ligands in asymmetric Lewis acid catalysis has been explored for the first time in the diethylzinc addition to aldehydes. The C2-symmetric ligand 1d showed an interesting catalytic behavior, which suggests the non-innocent participation of the triazole units. Thus, good enantioselectivities (up to 86% ee) were obtained by both the right selection of the substitution pattern at the triazole ring and the fine tuning of the reaction conditions. PB - © Georg Thieme Verlag DO - 10.1055/s-0031-1291009 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0031-1291009 ER -