What it is
The authors report a Pd/Sadphos-catalyzed dynamic kinetic asymmetric cascade dearomative Heck/Tsuji-Trost reaction of racemic phenolic biaryls with 1,3-dienes, driven by transient axial-to-point chirality induction and transfer. In a single catalytic transformation it delivers over 40 polycyclic spiro enones, each bearing three contiguous tertiary or quaternary stereocenters, in moderate to high yields. The products form with excellent regio-, diastereo-, and enantioselectivity, up to 99% ee.
Why it matters
Chiral spirocycles are prized scaffolds in drug discovery and asymmetric synthesis, but building polycyclic spiro compounds stereoselectively in one catalytic step has been an enduring challenge because of steric hindrance and electronic effects. This cascade assembles such structures in a single transformation, installing three contiguous tertiary or quaternary stereocenters with up to 99% ee. It also extends the reach of transient axial-to-point chirality transfer chemistry.
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Filed underAxial and Atropisomeric Chirality Synthesis, Asymmetric Synthesis and Catalysis, Catalytic C–H Functionalization Methods