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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|
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.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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