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Type: Artigo de periódico
Title: Quaternary Stereogenic Centers Through Enantioselective Heck Arylation Of Acyclic Olefins With Aryldiazonium Salts: Application In A Concise Synthesis Of (r)-verapamil.
Author: Oliveira, Caio C
Pfaltz, Andreas
Correia, Carlos Roque Duarte
Abstract: We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.
Subject: N,n Ligands
Enantioselective Heck
Quaternary Stereocenters
Citation: Angewandte Chemie (international Ed. In English). v. 54, n. 47, p. 14036-14039, 2015-Nov.
Rights: embargo
Identifier DOI: 10.1002/anie.201507927
Date Issue: 2015
Appears in Collections:Unicamp - Artigos e Outros Documentos

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