Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
The generation of quaternary and tertiary stereocenters on C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded with moderate to good yields (up to 81%), although with l...
| Authors: | , , , , |
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| Format: | article |
| Publication Date: | 2016 |
| Country: | España |
| Institution: | Universidad del País Vasco |
| Repository: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/64278 |
| Online Access: | http://hdl.handle.net/10810/64278 |
| Access Level: | Open access |
| Keyword: | C-C coupling Heck reaction palladium heterocycles asymmetric synthesis |
| Summary: | The generation of quaternary and tertiary stereocenters on C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded with moderate to good yields (up to 81%), although with low enantioselection when chiral phosphanes, such as (R)-BINAP, are used as ligands. However, enantiomerically pure 10-substituted pyrrolo[1,2-b]isoquinolines have been efficiently obtained through a diastereoselective approach using chiral non-racemic pyrrolidines as substrates, generating a tertiary stereocenter |
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