ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAsymmetric Diels-Alder reaction catalyzed by a chiral titanium reagentKoichi Narasaka, Nobuharu Iwasawa, Masayuki Inoue, Tohru Yamada, Masako Nakashima, and Jun SugimoriCite this: J. Am. Chem. Soc. 1989, 111, 14, 5340–5345Publication Date (Print):July 1, 1989Publication History Published online1 May 2002Published inissue 1 July 1989https://pubs.acs.org/doi/10.1021/ja00196a045https://doi.org/10.1021/ja00196a045research-articleACS PublicationsRequest...

Abstract The combined use of a catalytic amount silver acetate and stoichiometric DBU efficiently catalyzed the incorporation CO 2 under mild reaction conditions into wide range propargylic alcohols bearing terminal or an internal triple bond to afford corresponding cyclic carbonates in high‐to‐excellent yields. All obtained from were found be single isomers. geometries determined ( Z ) by X‐ray crystal structure analysis NOE experiments.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451...

The combined catalyst system of silver acetate with a chiral Schiff base ligand achieved asymmetric carbon dioxide incorporation into bispropargylic alcohols desymmetrization to afford the corresponding cyclic carbonates good-to-excellent enantiomeric excesses.

Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, required. It was found that a silver catalyst successfully promoted the incorporation CO2 into o-alkynylanilines to afford corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at activated C–C triple bond.

Abstract A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from reaction CO2 with propargylic alcohols amines, respectively, in high yields under mild conditions. It found that [3,3]-sigmatropic Meyer–Schuster-type rearrangement alcohol mediated by DMF to afford corresponding α,β-unsaturated carbonyl compounds yields. The silver salt combined chiral Schiff base ligand could be applied enantioselective chemical incorporation into...

Abstract In the presence of a bis(1,3-diketonato)nickel(II) complex, various olefins are directly monooxygenated into corresponding epoxides on treatment with atmospheric pressure oxygen or air and aldehydes. Especially, it is noted that bis[1,3-bis(p-methoxyphenyl)-1,3-propanedionato]nickel(II) behaves as an excellent catalyst in present epoxidation.

Asymmetric reduction of prochiral ketones with sodium borohydride proceeds in the presence catalytic amounts optically active β-oxoaldiminatocobalt(II) complexes 1 to corresponding secondary alcohols high chemical yields enantioselectivities (68–94% ee).

Abstract Enantioselective epoxidation of unfunctionalized olefins with combined use molecular oxygen, an oxidant, and pivalaldehyde, a reductant, was demonstrated in the presence catalytic amount optically active Mn(III)-salen complexes. Dihydronaphthalene derivatives were converted into corresponding epoxides good yields 60–77% enantiomeric excesses.

Abstract In the presence of a catalytic amount bis(acetylacetonato)cobalt(II), various olefins are hydrated with oxygen and secondary alcohol to afford corresponding alcohols together alkanes ketones via Oxidation-Reduction process. Effect additives in present hydration reaction shows that 2,6-lutidine 2-picoline inhibit production large extent result better yielding alcohols.

Abstract The silver-catalyzed carbon dioxide incorporation reaction into various propargylic amines proceeded under mild conditions to obtain the corresponding oxazolidinone derivatives in high excellent yields. geometry of C–C double bond product was confirmed be Z isomer by X-ray analysis.

In the presence of a catalytic amount silver salt with DBU under CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into corresponding α,β-unsaturated carbonyl compounds in high yield. An isotopic experiment using C18O2 revealed that carbon dioxide mediated rearrangement via an intramolecular nucleophilic attack on alkyne activated by catalyst.

Abstract Two highly enantioselective methods for hydrocyanation of aldehydes were developed by using chiral alkoxytitanium reagents. Treatment benzaldehyde with cyanotrimethylsilane in the presence a affords mandelonitrile good chemical and optical yields. By use cyanotitanium reagent generated situ from cyanotrimethylsilane, aliphatic are converted into corresponding cyanohydrins manner.

A catalytic amount of silver benzoate with 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was an effective system for the reaction carbon dioxide various ketones containing alkyne group at appropriate position. These reactions afforded corresponding γ-lactone derivatives in good to high yields under mild conditions.

Although 4-hydroxyquinolin-2(1H)-one derivatives have attracted much attention due to their biological benefits, conventional reactions under harsh heat conditions must be employed provide these key compounds. In the presence of a catalytic amount silver salt, various o-alkynylanilines were treated with carbon dioxide and base mild reaction afford corresponding in high yield.

Tetramic acid derivatives have been studied as biologically active heterocycle structures for pharmaceutical or agricultural chemicals. Conventional preparative approaches often require highly functionalized starting materials and harsh heating conditions in basic media. The present report provides a conceptually new synthetic strategy the synthesis of tetramic from easily available propargylic amines carbon dioxide with silver salt DBU under mild reaction conditions.

Abstract Highly substituted 2‐cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis‐acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting propargyl alcohol carbon dioxide in presence a silver catalyst. The stereochemistry 2‐cyclopentenone strictly controlled geometry alkene starting material. This method applicable for various substrates.

Abstract In the presence of a catalytic amount bis(1,3-diketonato)nickel(II) complex, trisubstituted and exo-terminal olefins or norbornene analogues are smoothly monooxygenated into corresponding epoxides in high to quantitative yields on treatment with aldehyde under an atmospheric pressure oxygen at room temperature.

Abstract Optically active N,N′-ethylenebis(α-alkoxycarbonyl-β-ketoimine) was found to be a new class of effective ligand manganese(III) complex catalyst for the asymmetric aerobic epoxidation simple olefins, such as 1,2-dihydronaphthalene derivatives, afford corresponding optically epoxides with good high enantioselectivities.

Abstract In the presence of a catalytic amount optically active ketoiminatocobalt complexes, enantioselective Henry reaction proceeded to afford β-nitro alcohols in good-to-high yields with high enantioselectivities.

Abstract Tris[1,3-bis(p-methoxyphenyl)-1,3-propanedionato]iron(III) (Fe(dmp)3) was found to be an excellent catalyst for oxygenation of a number olefinic compounds including styrene analogues and alcohols into the corresponding epoxides in good quantitative yields with combined use molecular oxygen aldehyde at room temperature.

Abstract In the presence of a catalytic amount nickel(II) complex coordinated with 1,3-diketone, various cyclic or acyclic ketones are converted into corresponding lactones esters by Baeyer–Villiger oxidation on treatment an atmospheric pressure molecular oxygen (oxidant) and aldehyde (reductant) at room temperature.

Abstract In the presence of a bis(1,3-diketonato)cobalt(II) complex, various olefins are converted to corresponding hydrated products according Markownikov rule on treatment with molecular oxygen in secondary alcohol (“oxidation–reduction hydration”). Removal water formed during hydration reaction, especially by azeotropic method, is remarkably effective improve yields based cobalt(II) catalyst as bis(trifluoroacetylacetonato)cobalt(II) (Co(tfa)2) or...

The atropo-enantioselective borohydride reduction with dynamic kinetic resolution of biaryl lactones was catalyzed by an optically active beta-ketoiminatocobalt(II) complex to afford compounds. Chiral HPLC analysis the starting performed at various temperatures determine suitable reaction conditions for resolution. Various types axially chiral compounds were obtained high enantioselectivity.