Dirhodium(II) tetrakis[ N-tetrafluorophthaloyl-( S)- tert-leucinate]: an exceptionally effective Rh(II) catalyst for enantiotopically selective aromatic C–H insertions of diazo ketoesters

Dirhodium(II) tetrakis[ N-tetrafluorophthaloyl-( S)- tert-leucinate], Rh 2[( S)-TFPTTL] 4, in which the phthalimido hydrogen atoms of the parent dirhodium(II) complex are substituted by fluorine atoms, dramatically enhances the reactivity and enantioselectivity (up to 97% ee) in intramolecular aroma...

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Published inTetrahedron: asymmetry Vol. 14; no. 7; pp. 817 - 821
Main Authors Tsutsui, Hideyuki, Yamaguchi, Yukiko, Kitagaki, Shinji, Nakamura, Seiichi, Anada, Masahiro, Hashimoto, Shunichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.04.2003
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
METAL CARBENE TRANSFORMATIONS
ORGANIC-SYNTHESIS
CARBON-HYDROGEN INSERTION
ASYMMETRIC-SYNTHESIS
RHODIUM
ENANTIOSELECTIVE SYNTHESIS
CYCLOPROPANATION
INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION
YLIDE FORMATION
CHIRAL CATALYSTS
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Summary:Dirhodium(II) tetrakis[ N-tetrafluorophthaloyl-( S)- tert-leucinate], Rh 2[( S)-TFPTTL] 4, in which the phthalimido hydrogen atoms of the parent dirhodium(II) complex are substituted by fluorine atoms, dramatically enhances the reactivity and enantioselectivity (up to 97% ee) in intramolecular aromatic C–H insertion reactions of methyl 4-alkyl-2-diazo-4,4-diphenyl-3-oxopropionates. Catalysis with the use of 0.001 mol% of Rh 2[( S)-TFPTTL] 4 has achieved the highest turnover number (up to 98,000 with the methyl substituent) ever recorded for chiral dirhodium(II) complex-catalyzed carbene transformations, without compromising the yield or enantioselectivity of the process. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00075-2