Enantiocontrol over Acyclic Quaternary Stereocenters by Acylative Organocatalyzed Kinetic Resolution

Xueyang Liu (1) , Jean-Marc Pons (1) , Valérie Monnier (2) , Laurence Charles (3) , Adrien Quintard (1) , Cyril Bressy (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 FSCM - Fédération des Sciences Chimiques de Marseille
3 ICR - Institut de Chimie Radicalaire

In the present paper, we described the efficient enantioselective kinetic resolution (KR) of racemic diastereocontrolled secondary alcohols bearing a quaternary stereocenter using a commercially available chiral isothiourea organocatalyst. This methodology is a general KR leading to the enantiocontrol of acyclic quaternary stereocenter with high levels of stereoselectivity (s up to 185) on a large scope. The hydroxyl function can easily serve as a traceless group by oxidation or reduction process.

Mots clés: Alcohols; Isothiourea; Kinetic resolution; Organocatalysis; Quaternary stereocenters

Domaines: Chimie organique

Xueyang Liu, Jean-Marc Pons, Valérie Monnier, Laurence Charles, Adrien Quintard, et al.. Enantiocontrol over Acyclic Quaternary Stereocenters by Acylative Organocatalyzed Kinetic Resolution. European Journal of Organic Chemistry, 2022, 2022 (6), pp.e202101475. ⟨10.1002/ejoc.202101475⟩. ⟨hal-03615865⟩