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Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution

Abstract : 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).
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https://hal.archives-ouvertes.fr/hal-03255245
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Submitted on : Monday, June 14, 2021 - 2:00:50 PM
Last modification on : Sunday, June 26, 2022 - 3:09:37 AM
Long-term archiving on: : Thursday, September 16, 2021 - 8:20:42 AM

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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, American Chemical Society, 2021, 23 (11), pp.4332 - 4336. ⟨10.1021/acs.orglett.1c01261⟩. ⟨hal-03255245⟩

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