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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: In this paper, the steric nature of the substituents at the stereogenic center of a tethered 1,3-dienes has been investigated and a model for the prediction of the extent and sense of diastereo induction was presented.
58 citations
TL;DR: When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of Pd(2)(dba)(3) x CHCl(3), 20 mol % of a bidentate ligand, and sodium acetate, carbapenam was produced in high yield.
Abstract: When a THF solution of β-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd2(dba)3·CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 °C for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a η3-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).
58 citations
TL;DR: The reaction proceeds under mild conditions via vinylidene complexes, and the activation parameters were determined by kinetic studies.
Abstract: Intramolecular [2 + 2] cycloaddition of two CC bonds in vinylidene complexes [Ru(η5-C9H7){CC(R)H}(PPh3){κ1-(P)-PPh2(C3H5)][BF4] affords cyclobutylidene complexes which can be also obtained by reaction of terminal alkynes with [Ru(η5-C9H7)(PPh3){κ3-(P,C,C)-PPh2(C3H5)}][PF6]. The reaction proceeds under mild conditions via vinylidene complexes, and the activation parameters were determined by kinetic studies.
58 citations
TL;DR: Treatment of (o-ethynyl)phenyl epoxides with TpRuPPh(3)(CH(3)CN)(2)PF(6) in hot toluene gave 2-naphthols or 1-alkylidene-2-indanones very selectively with isolated yields exceeding 72%, depending on the nature of the epoxide substituents.
Abstract: Treatment of (o-ethynyl)phenyl epoxides with TpRuPPh3(CH3CN)2PF6 (10 mol %) in hot toluene (100 °C, 3−6 h) gave 2-naphthols or 1-alkylidene-2-indanones very selectively with isolated yields exceeding 72%, depending on the nature of the epoxide substituents. Surprisingly, the reaction intermediate proved to be a ruthenium-π-ketene species that can be trapped efficiently by alcohol to give an ester compound. This phenomenon indicates a novel oxygen transfer from epoxide to its terminal alkyne catalyzed by a ruthenium complex. A plausible mechanism is proposed on the basis of reaction products and the deuterium-labeling experiment. The 2-naphthol products are thought to derive from 6-endo-dig cyclization of (o-alkenyl)phenyl ketene intermediates, whereas 1-alkylidene-2-indanones are given from the 5-endo-dig cyclization pathway.
58 citations
TL;DR: Treatment of a wide range of functionalized hydroxyallenic esters with 5 mol % Ph(3)PAuCl and AgOTf in CH(2)Cl(2), producing selectively 2-alkyl- and aryl-3-ethoxycarbonyl-2,5-dihydrofurans in good to excellent yield through intramolecular hydroalkoxylation by a 5-endo mode.
Abstract: Treatment of a wide range of functionalized hydroxyallenic esters with 5 mol % Ph3PAuCl and 5 mol % AgOTf in CH2Cl2 at 25 °C for 1 h produced selectively 2-alkyl- and aryl-3-ethoxycarbonyl-2,5-dihydrofurans in good to excellent yield through intramolecular hydroalkoxylation by a 5-endo mode.
58 citations