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

Chem Commun (Camb)

Department of Organic Chemistry, Faculty of Science, Charles University, 128 43 Prague, Czech Republic.

Published: September 2022

Herein, we report the first chiral phosphoric acid (CPA)-catalyzed asymmetric addition of α-fluoro(phenylsulfonyl)methane (FSM) derivatives to generated cyclic -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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Source
http://dx.doi.org/10.1039/d2cc02667hDOI Listing

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