Catalytic enantioselective synthesis of C1- and C2-symmetric spirobiindanones through counterion-directed enolate C-acylation

Journal article

A catalytic enantioselective route to C1- and C2- symmetric 2,2ʹ-spirobiindanones has been realized through an intramolecular enolate C-acylation. This reaction employs a chiral ammonium counterion to direct the acylation of an in situ generated ketone enolate with a pentafluorophenyl ester. This reaction constitutes the first example of a direct catalytic enantioselective Cacylation of a ketone and provides an efficient and highly enantioselective route to axially chiral spirobiindanediones. These products can be diastereoselectively derivatized, offering access to a range of functionalized spirocyclic architectures.

Authors: Rahemtulla, B; Clark, H; Smith, M

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Angewandte Chemie International Edition
• Volume: 55
• Issue: 42
• Pages: 13180–13183
• Publication date: 2016-01-01
• Acceptance date: 2016-08-25
• DOI: 10.1002/anie.201607731
• EISSN: 1521-3773
• ISSN: 1521-3757
• Keywords: phase-transfer; enantioselective synthesis; organocatalysis; axial chirality; counterion; C-acylation