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- Title
Generation of Tertiary and Quaternary Stereocentres through Palladium-Catalysed Intramolecular Heck-Type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2- b]isoquinolines.
- Authors
Azcargorta, Ane Rebolledo; Coya, Estíbaliz; Barbolla, Iratxe; Lete, Esther; Sotomayor, Nuria
- Abstract
The generation of quaternary and tertiary stereocentres at C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl-substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded in moderate to good yields (up to 81 %), but with low enantioselectivity when chiral phosphanes such as ( R)-BINAP were used as ligands. However, enantiomerically pure 10-substituted pyrrolo[1,2- b]isoquinolines were efficiently obtained by a diastereoselective approach using chiral nonracemic pyrrolidines as substrates, generating a tertiary stereocentre.
- Subjects
PALLADIUM catalysts; HECK reaction; ISOQUINOLINE synthesis; NITROGEN compound synthesis; PYRROLE derivatives; SUBSTITUENTS (Chemistry); HETEROCYCLIC compounds synthesis; ASYMMETRIC synthesis
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 11, p2054
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600082