Nothing Special   »   [go: up one dir, main page]

Matsubara et al., 2004 - Google Patents

Highly diastereo-and enantioselective reactions of enecarbamates with an aldehyde

Matsubara et al., 2004

Document ID
17670634645280368390
Author
Matsubara R
Vital P
Nakamura Y
Kiyohara H
Kobayashi S
Publication year
Publication venue
Tetrahedron

External Links

Snippet

Catalytic asymmetric addition reactions of enecarbamates with ethyl glyoxylate have been developed using CuClO4· 4CH3CN and a diimine ligand as the catalyst. Highly diastereo- and enantioselective addition reactions of α-mono-substituted enecarbamates have been …
Continue reading at www.sciencedirect.com (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/16—The ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/06—Systems containing only non-condensed rings with a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2102/00—Systems containing two condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

Similar Documents

Publication Publication Date Title
Matsubara et al. Highly diastereo-and enantioselective reactions of enecarbamates with an aldehyde
Hayashi et al. Asymmetric carbon carbon bond forming reactions catalyzed by chiral Schiff base—titanium alkoxide complexes
Arai et al. Phase-transfer-catalyzed asymmetric Darzens reaction
Arai et al. Asymmetric Darzens reaction utilizing chloromethyl phenyl sulfone under phase-transfer catalyzed conditions
Lo et al. Applications of planar-chiral heterocycles in enantioselective catalysis: Cu (I)/bisazaferrocene-catalyzed asymmetric ring expansion of oxetanes to tetrahydrofurans
Iseki et al. Asymmetric allenylation of aliphatic aldehydes catalyzed by a chiral formamide
Motoyama et al. Asymmetric hetero Diels–Alder reaction of Danishefsky's dienes and glyoxylates with chiral bis (oxazolinyl) phenylrhodium (III) aqua complexes, and its mechanistic studies
Huber et al. Consecutive catalytic electrophilic fluorination/amination of β-keto esters: toward α-fluoro-α-amino acids?
Asami et al. Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N, N-disubstituted aminomethyl) indoline
Narasaka et al. Enentio-and Diastereo-Selective Synthesis of (+)-Grandisol.
Hanyu et al. New chiral 1, 4-aminoalcohols derived from (+)-camphor and (−)-fenchone for the enantioselective addition of diethylzinc to aldehyde
Ooi et al. Asymmetric Synthesis of α‐Acyl‐γ‐butyrolactones Possessing All‐Carbon Quaternary Stereocenters by Phase‐Transfer‐Catalyzed Alkylation
Yato et al. Reduction of carboxylic esters to ethers with triethyl silane in the combined use of titanium tetrachloride and trimethylsilyl trifluoromethanesulfonate
Tanaka et al. Enantio-and diastereoselective construction of 4, 9-dimethylspiro [4.4] nonane-2, 7-dione using Rh-catalyzed asymmetric cyclization
Satoh et al. A novel method for the asymmetric synthesis of 4, 4-disubstituted 2-cyclopentenones from optically active 1-chlorovinyl p-tolyl sulfoxides and its application to the asymmetric total synthesis of (+)-α-cuparenone
Jaber et al. Tandem reactions catalyzed by lanthanide iodides. Part 1: Tandem Mukaiyama–Michael iminoaldol reactions
Imai et al. Insight into the Rh-catalyzed cyclization of dissymmetrically racemic (±)-3, 4-disubstituted 4-pentenal: regio-, diastereo-, enantioselectivity, and kinetic resolution
Montaña et al. Asymmetry induction on the [4C (4π)+ 3C (2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature
Konda et al. Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts
Jungong et al. Asymmetric intramolecular C–H insertion of sulfonyldiazoacetates catalyzed by Rh (II)
Yamagishi et al. Diastereoselective synthesis of β-substituted α-hydroxyphosphinates through hydrophosphinylation of α-heteroatom-substituted aldehydes
Ward et al. The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation
Zhong et al. Amino alcohols with the bicyclo [3.3. 0] octane scaffold as ligands for the catalytic enantioselective addition of diethylzinc to aldehydes
EP1049537B1 (en) Catalytic compositions and methods for asymmetric allylic alkylation
Lai et al. Diastereoselective synthesis of trans-3, 5-disubstituted dihydrofuran-2 (3H)-ones via SmI2-mediated reductive coupling of 2-alkylacrylates of N, N-diisopropyl-2-hydroxybenzamide with aldehydes