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Catalytic asymmetric addition to cyclic N -acyl-iminium: access to sulfone-bearing contiguous quaternary stereocenters.

Viraj A BhosaleIvana CísařováMartin KamlarJan Veselý
Published in: Chemical communications (Cambridge, England) (2022)
Herein, we report the first chiral phosphoric acid (CPA)-catalyzed asymmetric addition of α-fluoro(phenylsulfonyl)methane (FSM) derivatives to in situ generated cyclic N -acyliminium. This process enables metal-free expeditious access to sulfone and fluorine incorporating contiguous all substituted quaternary stereocenters ingrained in biorelevant isoindolinones in excellent stereoselectivities (up to 99% ee and up to 50 : 1 dr).
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