cheminform abstract: novel and stereocontrolled synthesis of enantiopure and polyalkyl substituted...

1998 pyridine derivatives pyridine derivatives R 0380 39 - 158 Novel and Stereocontrolled Synthesis of Enantiopure and Polyalkyl Substituted Piperidines. — Double nucleophilic addition of benzylamine to 7-oxo-2-enamides (I) results, after hydrogenation of the intermediate tetrahy- dropyridines, in diastereoselective formation of the piperidines (III) with three alkyl-substituted chiral centers. The method can be extended to ester (VI), which yields a diastereomeric mixture of cyanopiperidines. Diastereoselective substitution of the cyanide yields the chiral piperidine (X) with four stereocen- ters. — (SCHNEIDER, C.; BOERNER, C.; Synlett (1998) 6, 652-654; Inst. Org. Chem., Georg-August-Univ., D-37077 Goettingen, Germany; EN) 1

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Page 1: ChemInform Abstract: Novel and Stereocontrolled Synthesis of Enantiopure and Polyalkyl Substituted Piperidines

1998 pyridine derivatives

pyridine derivativesR 0380

39 - 158Novel and Stereocontrolled Synthesis of Enantiopure and PolyalkylSubstituted Piperidines. — Double nucleophilic addition of benzylamineto 7-oxo-2-enamides (I) results, after hydrogenation of the intermediate tetrahy-dropyridines, in diastereoselective formation of the piperidines (III) with threealkyl-substituted chiral centers. The method can be extended to ester (VI),which yields a diastereomeric mixture of cyanopiperidines. Diastereoselectivesubstitution of the cyanide yields the chiral piperidine (X) with four stereocen-ters. — (SCHNEIDER, C.; BOERNER, C.; Synlett (1998) 6, 652-654; Inst.Org. Chem., Georg-August-Univ., D-37077 Goettingen, Germany; EN)

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