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Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3877-80. doi: 10.1002/anie.201310517. Epub 2014 Mar 6.

Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Author information

1
Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT 06520 (USA).

Abstract

The first example of C alkylation of 1,2-dihydropyridines with alkyl triflates and Michael acceptors was developed to introduce quaternary carbon centers with high regio- and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeded with high diastereoselectivity. Carbon nucleophile addition results in an unprecedented level of substitution to provide piperidine rings with adjacent tetrasubstituted carbon atoms.

KEYWORDS:

alkylation; diastereoselectivity; heterocycles; reduction; synthetic methods

PMID:
24604837
PMCID:
PMC4058641
DOI:
10.1002/anie.201310517
[Indexed for MEDLINE]
Free PMC Article

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