Asymmetric pt(II)-catalyzed ene reactions: Counterion-dependent additive and diphosphine electronic effects

Catalysis of the glyoxylate-ene reaction by dicationic P2Pt(II) complexes is subject to anion-dependent additive effects. For [((S)-MeOBiphep)-Pt](OTf)(2) catalysts, acidic phenols such as 3-CF3-C6H3OH or C6F5OH provide substantial rate increases but do not affect the more active SbF6-based catalyst...

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Bibliographic Details
Published inOrganic letters Vol. 3; no. 8; pp. 1233 - 1236
Main Authors Koh, JH, Larsen, AO, Gagne, MR
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.04.2001
Subjects
Anions
Chemistry
Chemistry, Organic
Ions
Ligands
Models, Chemical
Phenol - chemistry
Phosphines - chemistry
Physical Sciences
Platinum - chemistry
Science & Technology
CHIRAL LEWIS-ACIDS
MICHAEL
PLATINUM(II)
1,3-DIPOLAR CYCLOADDITION
GLYOXYLATE
PALLADIUM(II)
C-H ACTIVATION
DERIVATIVES
CATALYSTS
BIS(OXAZOLINE) COPPER(II) COMPLEXES
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ISSN1523-7060
1523-7052
DOI10.1021/ol015702n

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Summary:Catalysis of the glyoxylate-ene reaction by dicationic P2Pt(II) complexes is subject to anion-dependent additive effects. For [((S)-MeOBiphep)-Pt](OTf)(2) catalysts, acidic phenols such as 3-CF3-C6H3OH or C6F5OH provide substantial rate increases but do not affect the more active SbF6-based catalysts. Enantioselectivity and reactivity also increased with diphosphine basicity, with 4-t-Bu-substituted MeOBiphep ligands yielding the highest enantioselectivities.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol015702n