Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp³-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold

Abstract

The first example of a chiral halogen-bond donor with a sp3-hybridized carbon–iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from (R)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (R)-1 worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (R)-1 as a catalyst to evaluate the asymmetric induction.

Keywords

• halogen-bond
• chiral halogen-bond donor
• Lewis acid
• organo-catalyst