TY - JOUR AU - Vízcaíno-Milla, Pascuala; Sansano, José M.; Nájera, Carmen; Fiser, Béla; Gómez-Bengoa, Enrique TI - Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides SN - 0039-7881 SN - 1437-210X PY - 2015 JO - Synthesis JF - Synthesis LA - EN VL - 47 IS - 15 SP - 2199 EP - 2206 ET - 2015/05/26 DA - 2015/07/21 KW - asymmetric organocatalysis KW - maleimides KW - succinimides KW - aldehydes KW - Michael addition AB - Chiral primary amines containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a pyrimidin-2-yl unit are synthesized and used as general organocatalysts for the Michael reaction of α-branched aldehydes to maleimides. The reaction takes place with 10 mol% organocatalyst loading and hexanedioic acid as cocatalyst in aqueous N,N-dimethylformamide at 10 °C affording the corresponding succinimides in good yields and enantioselectivities. DFT calculations support the stereochemical results and the role played by the solvents. PB - © Georg Thieme Verlag DO - 10.1055/s-0034-1380718 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0034-1380718 ER -