Rondot, ChristopheZhu, Jieping2010-11-252010-11-252010-11-25200510.1021/ol050334zhttps://infoscience.epfl.ch/handle/20.500.14299/58460A diastereoselective three-component synthesis of chiral 2-(1,2-diaminoalkyl)phenols from an electron-rich phenol, an amine, and a chiral alpha -N,N-dibenzylamino aldehyde is developed. The diastereoselectivity of this phenolic Mannich reaction is temp.-dependent,and either anti or syn diastereomer can be prepd. by controlling the reaction conditions. Low reaction temp. (-20 DegC) favors the formation of anti adduct, whereas higher temp. (60 DegC) under otherwise identical conditions produces mainly the syn isomer. [on SciFinder (R)]Amines Role: SPN (Synthetic preparation)PREP (Preparation) (diamines; temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction); Asymmetric synthesis and induction; Mannich reaction; Temperature (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction); Aldehydes; Amines; Phenols Role: RCT (Reactant)RACT (Reactant or reagent) (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction)stereoselective Mannich phenol amine amino aldehyde temptext::journal::journal article::research article