Enantioselective Sequential Catalytic Arylation‐Fukuyama Cross‐coupling of 1,1‐Biszincioalkane Linchpins - Sorbonne Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2023

Enantioselective Sequential Catalytic Arylation‐Fukuyama Cross‐coupling of 1,1‐Biszincioalkane Linchpins

Abstract

1,1‐Bis(iodozincio)alkanes are used as dinucleophilic linchpins in an enantioselective double cross‐coupling reaction sequence involving aryl iodides and then thioesters. The two catalytic C−C bond‐forming reactions are achieved in the same pot through two distinct palladium‐based catalytic systems: a first non‐enantioselective one delivering configurationally labile secondary benzylzinc species from an achiral precursor, and a second enantioconvergent one that operates a highly efficient dynamic kinetic resolution of the racemic intermediates. This strategy, new in the area of asymmetric synthesis through two consecutive electrophilic substitution reactions of geminated C(sp 3 )‐organodimetallics, provides useful methodology to access in a modular fashion acyclic α ‐disubstituted ketone products with very high enantiomeric purity.
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Dates and versions

hal-04197445 , version 1 (08-09-2023)

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Federico Banchini, Baptiste Leroux, Erwan Le Gall, Marc Presset, Olivier Jackowski, et al.. Enantioselective Sequential Catalytic Arylation‐Fukuyama Cross‐coupling of 1,1‐Biszincioalkane Linchpins. Chemistry - A European Journal, 2023, 29 (36), pp.e202301084. ⟨10.1002/chem.202301084⟩. ⟨hal-04197445⟩
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