Regio‐ and Stereoselective 1, 2‐Dihydropyridine Alkylation/Addition Sequence for the Synthesis of Piperidines with Quaternary Centers1. Issue 15 (6th March 2014)

• Record Type: Journal Article
• Authors: Duttwyler, Simon; Chen, Shuming; Lu, Colin; Mercado, Brandon Q.; Bergman, Robert G.; Ellman, Jonathan A.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 15(2014)
• Page Start: 3877
• Page End: 3880
• Publication Date: 2014-03-06
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201310517
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>