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Regio‐ and Stereoselective 1,2‐Dihydropyridine Alkylation/Addition Sequence for the Synthesis of Piperidines with Quaternary Centers
Author(s) -
Duttwyler Simon,
Chen Shuming,
Lu Colin,
Mercado Brandon Q.,
Bergman Robert G.,
Ellman Jonathan A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310517
Subject(s) - alkylation , iminium , chemistry , piperidine , nucleophile , stereoselectivity , dihydropyridine , alkyl , hydride , nucleophilic substitution , medicinal chemistry , stereochemistry , ion , organic chemistry , catalysis , hydrogen , calcium
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.