Synthesis of New C2- Symmetric Fluoren-9-ylidene Malonate Derived Bis(oxazoline) Ligands and Their Application in Friedel-Crafts Reactions

Abstract

A series of new C2-symmetric fluoren-9-ylidene malonate-derived bis(oxazoline) ligands were synthesized from fluoren-9-ylidene malonate and enantiomerically pure amino alcohols via a convenient route. Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)2 complex of a fluoren-9-ylidene malonate-derived bis(oxazoline) bearing a phenyl group showed moderate to good enantioselectivity (up to 88% ee).

Keywords

• bis(oxazoline)
• fluoren-9-ylidene
• asymmetric catalysis
• Friedel-Crafts