[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

Tomioka et al., 1981 - Google Patents

Highly Stereoselective Construction of Chiral Quaternary Carbon: Asymmetric Synthesis of β, β-Disubstituted γ-Butyrolactones

Tomioka et al., 1981

Document ID
2075606510011002221
Author
Tomioka K
Cho Y
Sato F
Koga K
Publication year
Publication venue
Chemistry Letters

External Links

Snippet

Asymmetric synthesis of β, β-disubstituted γ-butyrolactones was carried out in highly stereoselective and predictable way, by means of sequential dialkylation of (S)-γ- trityloxymethyl-γ-butyrolactone followed by lactone carbonyl transposition. Application to the …
Continue reading at academic.oup.com (other versions)

Classifications

    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • 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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. -COOH
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring heteroatom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals substituted by singly or doubly bound oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring heteroatom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Monocyclic
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2102/00—Systems containing two condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups

Similar Documents

Publication Publication Date Title
Rychnovsky et al. Stereocontrolled synthesis of cis-2, 5-disubstituted tetrahydrofurans and cis-and trans-linalyl oxides
Hoffmann et al. Stereoselective synthesis of alcohols, XXXI: Stereoselective C C bond formation using chiral Z‐pentenylboronates
Wang et al. Model studies of the stereoelectronic effect in Rh (II) mediated carbenoid CH insertion reactions
Bernardi et al. Norephedrine-derived 2-alkenyloxazolidines: stereochemistry of cyclization and allylic stereocenter directed asymmetric conjugate addition
Ibuka et al. Very high chemoselective, regioselective, and E-stereoselective 1, 3-chirality transfer involving reaction of acyclic (E)-and (Z)-. gamma.-mesyloxy. alpha.,. beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral. alpha.-alkyl (E)-. beta.,. gamma.-enoates and (E)-allylic alcohols with high optical purity
Delay et al. Syntheses and Absolute Configuration of (E)‐and (Z)‐α‐Bisabolenes
Brown et al. Organoboranes. 38. A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo [3.3. 1] nonanes to aldehydes and ketones: an exceptionally chemoselective synthesis of propargylic alcohols
Jacobi et al. Bis heteroannulation. 4. Facile syntheses of methylene acids, methylbutenolides,. alpha.-methyl-. gamma.-lactones, and related materials. Total syntheses of (.+-.)-ligularone and (.+-.)-petasalbine
Brown et al. Highly efficient asymmetric reduction of. alpha.-tertiary alkyl ketones with diisopinocampheylchloroborane
AU612449B2 (en) New 3,5-dihydroxy carboxylic acids and derivatives thereof, a process for the preparation thereof, the use thereof as pharmaceuticals, pharmaceutical products and intermediates
Tanigawa et al. Regio-and stereoselective. gamma. substitution of allylic alcohols with alkyllithium compounds by using N, N-methylphenylaminotributylphosphonium iodide. Anti stereochemistry of SN2'reaction
Nishikimi et al. Synthetic studies of azadirachtin. Synthesis of the cyclic acetal intermediate in the naturally occurring form
Tomioka et al. Highly Stereoselective Construction of Chiral Quaternary Carbon: Asymmetric Synthesis of β, β-Disubstituted γ-Butyrolactones
Shioiri et al. New methods and reagents in organic synthesis. 2. A facile conversion of alkyl aryl ketones to. alpha.-arylalkanoic acids using diphenyl phosphorazidate. Its application to a new synthesis of ibuprofen and naproxen, nonsteroidal antiinflammatory agents
Pirkle et al. Enantiomerically pure lactones. 2. Approaches to cis or trans multicyclic lactones
US5750794A (en) Process for preparing chiral tetralone
Vaultier et al. Reaction of azomethine ylides with sulfur ylides. Novel azetidine synthesis
TAKAHASHI et al. Enantioselective darzens reaction: asymmetric synthesis of trans-glycidic esters mediated by chiral lithium amides
Fuganti et al. Stereochemistry of Baker's yeast mediated reduction of α, β-unsaturated δ-lactones in the goniothalamin series.
Biftu et al. Syntheses of lignans from 2, 3-diarolybutanes
Rupprecht et al. Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans
Price et al. Improved synthesis of 3, 4-disubstituted furans: use of phase-transfer conditions
House et al. Synthesis of cis-and trans-Derivatives of 1a-Carboxymethyl-8-methylhexahydrofluorenone
Kido et al. Carbocyclic construction by the [2, 3] sigmatropic rearrangement of cyclic sulfonium ylides. A new entry for the stereoselective synthesis of substituted cyclohexanones
Nishida et al. Synthesis of heavily substituted cyclopropylethylenes by titanium (0) catalyzed cross-coupling of ketones. Restricted rotation in 1, 1-dicyclopropyl-2, 2-di (2-propyl) ethylene