An improved method for chiral oxazaborolidine-catalyzed reduction of 4-chromanone analogs and MK-0499

Addition of isopropanol to the stoichiometric reduction of ketones 4 – 8 using oxazaborolidine-borane complex 3 or the oxazaborolidine-catalyzed reduction of 4-chromanone analogs ( 1, 7 – 9) enhances the enantioselectivity of the reduction. Addition of isopropanol to the stoichiometric reduction or...

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Published inTetrahedron letters Vol. 35; no. 35; pp. 6409 - 6412
Main Authors Shi, Yao-Jun, Cai, Dongwei, Dolling, U.-H., Douglas, Alan W., Tschaen, David M., Verhoeven, Thomas R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.08.1994
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ENANTIOSELECTIVE REDUCTION
KETONES
REAGENTS
BORANE
ASYMMETRIC REDUCTION
Enantioselectivity
Nitrogen heterocycle
Calcium antagonist
Alcohol
Ionic channel
Oxygen heterocycle
Ketone
Spiran
Oxygen nitrogen boron heterocycle
Chemical reduction
Amine borane
Six membered ring
Bicyclic compound
Aromatic compound
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Summary:Addition of isopropanol to the stoichiometric reduction of ketones 4 – 8 using oxazaborolidine-borane complex 3 or the oxazaborolidine-catalyzed reduction of 4-chromanone analogs ( 1, 7 – 9) enhances the enantioselectivity of the reduction. Addition of isopropanol to the stoichiometric reduction or the oxazaborolidine-catalyzed reduction of 4-chromanone analogs enhances the enantioselectivity of the reduction.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)78232-3