A Chiral Scandium Catalyst for Enantioselective Diels-Alder Reactions

A chiral scandium catalyst, prepared from scandium trifluoromethanesulfonate (Sc(OTf)(3)), (R)-(+)1,1'-bi-2-naphthol, and a tertiary amine in dichloromethane, was quite effective in the enantioselective Diels-Alder reactions of acyl-1,3-oxazolidin-2-ones with dienes, and the corresponding Diels...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 59; no. 14; pp. 3758 - 3759
Main Authors Kobayashi, Shu, Araki, Mitsuharu, Hachiya, Iwao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.1994
Amer Chemical Soc
Subjects
Catalysis
Catalysts: preparations and properties
Chemistry
Chemistry, Organic
Exact sciences and technology
General and physical chemistry
Physical Sciences
Science & Technology
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
REAGENT
SYSTEM
ALDOL
TRIFLUOROMETHANESULFONATE SC(OTF)3
LEWIS-ACID
COMPLEXES
Mixed catalyst
Five membered ring
Catalytic reaction
Enantioselectivity
Diels Alder addition
Chiral compound
Experimental study
Scandium Compounds
Tertiary amine
Transition metal Organic compounds
Enone
Catalyst
Oxygen nitrogen heterocycle
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Summary:A chiral scandium catalyst, prepared from scandium trifluoromethanesulfonate (Sc(OTf)(3)), (R)-(+)1,1'-bi-2-naphthol, and a tertiary amine in dichloromethane, was quite effective in the enantioselective Diels-Alder reactions of acyl-1,3-oxazolidin-2-ones with dienes, and the corresponding Diels-Alder adducts were obtained in high yields with high diastereo- and enantioselectivities.
Bibliography:istex:A4A9541250EA24A50633C9CA0A3813F8CDF8F34F
ark:/67375/TPS-9H9PNZP2-6
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00093a004