Synthesis of Chiral Vicinal Diamines by Highly Diastereoselective Three-Component Phenolic Mannich Reaction: Temperature-Dependent Stereodivergency

A 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)]


Published in:
Organic Letters, 7, 8, 1641-1644
Year:
2005
Keywords:
Note:
CAN 142:446959
25-10
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
54761-04-5 (Ytterbium(III) triflate) Role: CAT (Catalyst use), USES (Uses) (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction); 84-85-5 (4-Methoxy-1-naphthol); 90-15-3 (1-Naphthol); 100-46-9 (Benzylamine); 104-94-9 (p-Anisidine); 135-19-3 (2-Naphthol); 533-31-3 (Sesamol); 2393-23-9 (4-Methoxybenzylamine); 3966-32-3; 26164-26-1 ((S)-alpha -Methoxyphenyl acetic acid); 101711-55-1 (2-tert-Butyldimethylsilyloxyethylamine); 111060-63-0 (L-N,N-Dibenzylalaninal); 111060-64-1 (L-N,N-Dibenzylphenylalaninal); 125654-82-2 Role: RCT (Reactant), RACT (Reactant or reagent) (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction); 851314-64-2P; 851314-73-3P; 851314-74-4P; 851314-75-5P; 851314-78-8P; 851314-79-9P; 867339-07-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction); 851314-65-3P; 851314-66-4P; 851314-67-5P; 851314-68-6P; 851314-69-7P; 851314-70-0P; 851314-71-1P; 851314-72-2P; 851314-76-6P; 851314-77-7P; 851314-80-2P; 851314-81-3P; 851314-82-4P Role: SPN (Synthetic preparation), PREP (Preparation) (temp.-dependent stereodivergency in the synthesis of chiral vicinal diamines by a three-component phenolic Mannich reaction)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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