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Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution
- Source :
- Organic Letters, Organic Letters, 2021, 23 (11), pp.4332-4336. ⟨10.1021/acs.orglett.1c01261⟩, Organic Letters, American Chemical Society, 2021, 23 (11), pp.4332-4336. ⟨10.1021/acs.orglett.1c01261⟩
- Publication Year :
- 2021
-
Abstract
- International audience; 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).
- Subjects :
- Kinetic Resolution
Alcohol
Enantioselectivity
010402 general chemistry
01 natural sciences
Biochemistry
Kinetic resolution
Catalysis
Acylation
chemistry.chemical_compound
polycyclic compounds
Organic chemistry
Lewis acids and bases
Physical and Theoretical Chemistry
010405 organic chemistry
Chemistry
Organocatalysis
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Tertiary Alcohols
[CHIM.CATA]Chemical Sciences/Catalysis
0104 chemical sciences
Lewis Base
Organic synthesis
Tertiary alcohols
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 23
- Issue :
- 11
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....95954ddee3c7397e6b65b2bb74e44c9d
- Full Text :
- https://doi.org/10.1021/acs.orglett.1c01261⟩