Oliveira, Caio C. and Pfaltz, Andreas and Correia, Carlos Roque Duarte. (2015) Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil. Angewandte Chemie International Edition, 54 (47). pp. 14036-14039.
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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.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Synthetische organische Chemie (Pfaltz) |
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UniBasel Contributors: | Pfaltz, Andreas |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Wiley |
ISSN: | 1433-7851 |
e-ISSN: | 1521-3773 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Language: | English |
Identification Number: |
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edoc DOI: | |
Last Modified: | 23 Oct 2019 13:52 |
Deposited On: | 10 May 2016 11:44 |
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