Abstract
[figure: see text] Novel chiral P,N-ligands were synthesized from (1S)-(+)-ketopinic acid using palladium-catalyzed coupling reaction of a vinyl triflate and either a diarylphosphine or a dialkylphosphine as the key step. Palladium complexes of these ligands are efficient catalysts for asymmetric Heck reaction between aryl or alkenyl triflates and cyclic alkenes. Products were obtained with good to excellent enantioselectivity from arylation and alkenylation of 1,2-dihydrofuran, cyclopentene, and 4,7-dihydro-1,3-dioxepin.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkenes / chemistry
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Bridged-Ring Compounds*
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Chemistry, Organic / methods
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Ketones*
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Ligands
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Models, Molecular
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Molecular Conformation
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Molecular Structure
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Oxazoles / chemical synthesis*
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Oxazoles / chemistry
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Palladium
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Phosphines / chemical synthesis*
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Phosphines / chemistry
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Alkenes
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Bridged-Ring Compounds
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Ketones
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Ligands
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Oxazoles
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Phosphines
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ketopinic acid
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Palladium