Chiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols

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Catalytic enantioselective desymmetrization of meso-2-substituted glycerols has been developed to secure a novel synthetic route to chiral tertiary alcohols. The transformation has been realized by monobenzoylation using benzoyl chloride and triethylamine in the presence of the imine ligand (25)-CuCl2 complex in THF at ambient temperature. The desymmetrization turned out to be greatly dependent on acylating reagent, base, solvent, and needless to say, catalyst. Extensive screening of chiral ligands led us to combine bromopyridinecarboxaldehyde 1 and phenyloxazoline amine 12 derived from tert-leucine, the bromo and phenyl substituents of which proved to be indispensable. All of the substrates have been desymmetrized to the corresponding monobenzoates with high enantioselectivity up to 96% enantiomeric excess. The catalytic system allows broad structural diversity of substrates and its synthetic versatility has been demonstrated by an efficient synthetic route to a known key precursor 68 of triazole antifungals.
Publisher
NATL ACAD SCIENCES
Issue Date
2007-01
Language
English
Article Type
Article
Keywords

ASYMMETRIC ADDITION; ENZYMATIC ASYMMETRIZATION; QUATERNARY STEREOCENTERS; KINETIC RESOLUTION; ALKYLZINC REAGENTS; ALIPHATIC-KETONES; ANTIFUNGAL AGENTS; KEY INTERMEDIATE; HIGHLY EFFICIENT; ALDOL ADDITIONS

Citation

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, v.104, no.5, pp.1471 - 1475

ISSN
0027-8424
DOI
10.1073/pnas.0607865104
URI
http://hdl.handle.net/10203/90994
Appears in Collection
CH-Journal Papers(저널논문)
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