Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution

Titouan Desrues (1) , Xueyang Liu (1) , Jean-Marc Pons (1) , Valérie Monnier (2) , Jean-Arthur Amalian (3) , 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

The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed selective acylation of adjacent secondary alcohols. This transformation enables the kinetic resolution (KR) of easily prepared racemic diastereoenriched secondary/tertiary diols providing both monoesters and starting diols in highly enantioenriched forms (s-value >200).

Mots clés: Organocatalysis; Lewis Base; Kinetic Resolution; Tertiary Alcohols; Enantioselectivity

Domaines: Chimie organique; Catalyse

Titouan Desrues, Xueyang Liu, Jean-Marc Pons, Valérie Monnier, Jean-Arthur Amalian, et al.. Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution. Organic Letters, 2021, 23 (11), pp.4332 - 4336. ⟨10.1021/acs.orglett.1c01261⟩. ⟨hal-03255245⟩