[go: up one dir, main page]

Kita et al., 1994 - Google Patents

First highly asymmetric Pummerer-type reaction in chiral, non-racemic acyclic sulfoxides induced by O-silylated ketene acetal

Kita et al., 1994

View PDF
Document ID
6462382961867089113
Author
Kita Y
Shibata N
Yoshida N
Fujita S
Publication year
Publication venue
Journal of the Chemical Society, Perkin Transactions 1

External Links

Snippet

Various types of syn-and anti-β-substituted sulfoxides 6b–e, g reacted with ketene tert- butyldimethylsilyl acetal 2 in the presence of a catalytic amount of zinc iodide in acetonitrile to give high yields of the corresponding α-siloxy sulfides 7b–e, g stereoselectively. Similarly …
Continue reading at nitech.repo.nii.ac.jp (PDF) (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C-Si linkages
    • C07F7/18—Compounds having one or more C-Si linkages as well as one or more C-O-Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1812—Compounds having Si-O-C linkages having (C1)a-Si-(OC2)b linkages, a and b each being >=1 and a+b = 4, C1 and C2 being hydrocarbon or substituted hydrocarbon radicals
    • C07F7/1844—Compounds having Si-O-C linkages having (C1)a-Si-(OC2)b linkages, a and b each being >=1 and a+b = 4, C1 and C2 being hydrocarbon or substituted hydrocarbon radicals a being 3, b being 1
    • C07F7/1848—C1 being an unsubstituted acyclic saturated hydrocarbon radical containing less than six carbon atoms, a benzyl radical, a phenyl radical, or a methyl substituted phenyl radical
    • C07F7/1856—C2 containing cycloaliphatic, heterocyclic or condensed aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/04—Five-membered rings having the hetero atoms in position 1,2, e.g. lipoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR

Similar Documents

Publication Publication Date Title
Arai et al. Phase-transfer-catalyzed asymmetric Darzens reaction
US5929232A (en) Stereoselective ring opening reactions
Dauvergne et al. Synthesis of 4-azacyclopent-2-enones and 5, 5-dialkyl-4-azacyclopent-2-enones
Pirkle et al. Synthesis and enantiomeric purity determination of the optically active epoxide disparlure, sex pheromone of the gypsy moth
ES2875551T3 (en) Method for preparing optically pure (R) -4-n-propyl-dihydrofuran-2 (3H) -one
US4751299A (en) Optically active β-lactams and method of their production
EP0912495A1 (en) Asymetric synthesis of chiral beta-amino acids
Palomo et al. Asymmetric 1, 4-addition of higher order silylcuprates to Oppolzer's N-enoyl sultams
Kita et al. First highly asymmetric Pummerer-type reaction in chiral, non-racemic acyclic sulfoxides induced by O-silylated ketene acetal
Gouault-Bironneau et al. Thiophilic nucleophilic trifluoromethylation of α-substituted dithioesters. Access to S-trifluoromethyl ketene dithioacetals and their reactivity with electrophilic species
NZ243972A (en) Beta-phenylisoserine derivatives and taxane derivatives prepared therefrom
Strijtveen et al. Synthesis and determination of enantiomeric excesses of non-racemic tert-thiols derived from chiral secondary α-mercaptocarboxylic acids
EP1940387B1 (en) Process for the stereoselective preparation of (-)-halofenate and intermediates thereof
US5731448A (en) (+) and (-)-8-chloro-6-sulfonyloxy-octanoic acid, its derivatives, and methods for making
EP2513030B2 (en) Beta-gamma unsaturated esters and process of production of beta-gamma unsaturated esters.
Bhuniya et al. Enantioselective Deprotonation of Cyclohexene Oxide to (R)-2-Cyclohexen-1-ol
Fujiwara et al. An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters
Katagiri et al. Efficient synthesis of an optically pure β-bromo-β, β-difluoroalanine derivative, a general precursor for β, β-difluoroamino acids
JP3839857B2 (en) Method for producing ether type thiophospholipid compound
Annunziata et al. Reaction of lithioenamines with sulphinate esters. Stereospecific and stereoselective synthesis of β-enamino and β-imino sulphoxides
Ma et al. Photochemical Studies on 5‐Methylbicyclo [1.1. 1] pentane Derivatives: p‐Orbital Overlap Controlled Enantioselectivity
Akai et al. Chemistry of silylketenes: a simple preparation of α-silyl-α-stannylacetic esters and their stereoselective Reformatsky-type reaction with aldehydes or aldimines
Unger et al. Diastero-and enantioselective intramolecular carbometalation reaction
JP3979743B2 (en) Method for producing optically active vinyl phosphine oxide
JPH023793B2 (en)