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- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes abstract "Asymmetric addition of alkynylzinc compounds to aldehydes is an enantioselective chemical reaction where alkynylzinc reagents react with aldehydes to generate propargyl alcohols. Propargyl alcohols are versatile precursors to various complex molecules making the asymmetric addition of alkynylzinc compounds to aldehydes a particularly useful method for the synthesis of natural products and pharmaceutical drugs. For example, Carreira and co-workers have used this asymmetric reaction for the synthesis of natural product Leucascandrolide A, one of the first powerfully bioactive metabolites isolated from a calcareous sponge. Various chiral ligands have been developed for the asymmetric addition of alkynylzinc compounds to aldehydes. Because of the acidity of the terminal alkynyl proton, the alkynylzinc compounds can be generated in situ from reaction of terminal alkynes with alkylzincs or Zn(OTf)2.The first example of catalytic asymmetric addition of alkynylzinc compounds to aldehydes was reported by Kenso Soai and co-workers in 1990. In their experiments, chiral amino alcohols and amines (A to C in Figure \"Examples of ligands used in asymmetric addition of alkynylzinc compounds to aldehydes\") were used as ligands, and the alkynylzinc reagent was prepared from reaction of alkyne with diethylzinc. Although the yields were high, but the highest enantiomeric excess achieved was only 34% with 5 mol% ligand loading. Erick Carreira and co-workers reported high enantiomeric excess using a chiral amino alcohol, N-methylephedrine (D). Stoichiometric amount of D was used in their reactions, and up to 99% of enantiomeric excess was achieved at room temperature for a broad range of aldehydes. In Carreira’s experiments, the alkynylzinc reagent was generated from the reaction of alkyne with Zn(OTf)2 in the presence of an amine base.".
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes thumbnail Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes..png?width=300.
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- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageRevisionID "684247837".
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Aldehyde.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Alkyne.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Calcareous_sponge.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Category:Chemical_reactions.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Diethylzinc.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Enantiomeric_excess.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink N-Methylephedrine.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Natural_product.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Pharmaceutical_drug.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink Propargyl.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink File:Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes..png.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLink File:Examples_of_ligands_used_in_asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes..png.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageWikiLinkText "Asymmetric addition of alkynylzinc compounds to aldehydes".
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes wikiPageUsesTemplate Template:Reflist.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes subject Category:Chemical_reactions.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes hypernym Reaction.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes type Disease.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes comment "Asymmetric addition of alkynylzinc compounds to aldehydes is an enantioselective chemical reaction where alkynylzinc reagents react with aldehydes to generate propargyl alcohols. Propargyl alcohols are versatile precursors to various complex molecules making the asymmetric addition of alkynylzinc compounds to aldehydes a particularly useful method for the synthesis of natural products and pharmaceutical drugs.".
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes label "Asymmetric addition of alkynylzinc compounds to aldehydes".
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- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes depiction Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes..png.
- Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes isPrimaryTopicOf Asymmetric_addition_of_alkynylzinc_compounds_to_aldehydes.