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JoyaPhos: An Atropisomeric Teraryl Monophosphine Ligand
Author(s) -
Castrogiovanni Alessandro,
Lotter Dominik,
Bissegger Fabian R.,
Sparr Christof
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001269
Subject(s) - computer science , chemistry
Abstract A topologically well‐defined atropisomeric teraryl monophosphine ligand system, prepared by a highly stereoselective arene‐forming aldol condensation combined with a direct ester‐to‐anthracene transformation, is described herein. The ligands were evaluated for gold(I)‐catalyzed [2+2] cycloaddition and cycloisomerization reactions as well as a unique intramolecular Pd‐catalyzed C−N cross‐coupling for the atroposelective synthesis of a N ‐aryl‐indoline bearing a C−N stereogenic axis. The ligand structure induced up to 95:5 stereoselectivity in the asymmetric allylic alkylation reaction and features an interesting dynamic behavior as observed by X‐ray crystallographic studies.