Ortho‐Quinone Methides as Reactive Intermediates in Asymmetric Brønsted Acid Catalyzed Cycloadditions with Unactivated Alkenes by Exclusive Activation of the Electrophile |
| |
| Authors: | MSc Chien‐Chi Hsiao Dr Sadiya Raja MSc Hsuan‐Hung Liao Prof?Dr Magnus Rueping |
| |
| Institution: | Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen (Germany) |
| |
| Abstract: | An efficient method for the highly enantioselective synthesis of chiral chromanes bearing multiple stereogenic centers was developed. A chiral BINOL‐based N‐triflylphosphoramide proved to be an effective catalyst for the in situ generation of ortho‐quinone methides (o‐QMs) and their subsequent cycloaddition reaction with unactivated alkenes provided chromanes with excellent diastereo‐ and enantioselectivity. |
| |
| Keywords: | chromanes cycloaddition homogeneous catalysis n‐triflylphosphoramide ortho‐quinone methide |
|
