Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2020

Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds

Résumé

In this manuscript, a simple and efficient sulfa-Michael addition reaction of aryl thiols to trisubstituted α-fluoro-α,β-unsaturated esters both in racemic and, for the first time, in enantioselective version is reported. The commercially available dimer of cinchona derivatives (DHQ)2PYR was used as catalyst. This strategy showed a great tolerance for various substrates and substituents, providing fair to excellent yields, moderate to excellent diastereoselectivities (2:1 to > 99:1) and low to good enantioselectivities (2 to 87%). The reaction has been applied to the synthesis of fluorinated analogues of Diltiazem and Tiazesim, both therapeutic agents.

Domaines

Chimie
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Dates et versions

hal-03004699 , version 1 (08-12-2020)

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Citer

Xin Huang, Emilie David, Philippe Jubault, Tatiana Besset, Samuel Couve-Bonnaire. Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds. Journal of Organic Chemistry, 2020, 85 (21), pp.14055-14067. ⟨10.1021/acs.joc.0c02081⟩. ⟨hal-03004699⟩
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