Catalytic Intramolecular Hydroamination of Substituted Aminoallenes by Chiral Titanium Amino-Alcohol Complexes

Citations Over TimeTop 10% of 2004 papers

Abstract

Intramolecular hydroamination of aminoallenes is catalyzed by titanium complexes with a number of chiral amino alcohols. The ring-closing reaction of hepta-4,5-dienylamine at 110 °C with 5 mol % catalyst gives a mixture of 6-ethyl-2,3,4,5-tetrahydropyridine (14−33%) and both Z- and E-2-propenylpyrrolidine (67−86%). However, the ring-closing reaction of 6-methylhepta-4,5-dienylamine at 135 °C with 5 mol % catalyst gives exclusively 2-(2-methylpropenyl)pyrrolidine. The pyrrolidine products are obtained with enantiomeric excesses up to 16%.

Related Papers

• → Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings(1996)47 cited
• → Enantiomeric enrichment by the use of density differences between racemic compounds and optically active enantiomers(1995)16 cited
• → Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis(2013)23 cited
• → Resolution of Optical Isomers by Thin‐Layer Chromatography: Enantiomeric Purity of Methyldopa. Dünnschichtchromatographische Enantiomerentrennung: Enantiomere Reinheit von Methyldopa(1986)43 cited
• → Colour indicator for enantiomeric excess and assignment of the configuration of the major enantiomer of an amino acid ester(2002)26 cited