Premium
Generation of Tertiary and Quaternary Stereocentres through Palladium‐Catalysed Intramolecular Heck‐Type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2‐ b ]isoquinolines
Author(s) -
Azcargorta Ane Rebolledo,
Coya Estíbaliz,
Barbolla Iratxe,
Lete Esther,
Sotomayor Nuria
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600082
Subject(s) - chemistry , intramolecular force , enantioselective synthesis , palladium , heck reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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.