Showing papers on "Ferrier rearrangement published in 2009"
TL;DR: Highly anti- and enantioselective synthesis of beta-amino aldehydes having an aliphatic substituent at the beta-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis-Ferrier rearrangement.
Abstract: Highly anti- and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.
117 citations
TL;DR: Gold(III)chloride in catalytic amounts activates 3,4,6-tri- O -acetyl-d -glucal, 3, 4, 6-tri O −acetyl -d -galactal, and 3.4,di-O -acetylon- l -rhamnal efficiently as discussed by the authors.
54 citations
TL;DR: In this paper, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed, using ZnCl2 impregnated on activated alumina.
42 citations
TL;DR: The use of zirconium compounds as a promoter and catalyst for many important organic reactions including addition reactions such as Michael reac- tion, aldo reaction, Strecker reaction and carbometalation was reviewed in this article.
Abstract: From a viewpoint of synthetic organic chemistry, the recent developments and applications of zirconium com- pounds as promoter and catalyst for many important organic reactions including addition reactions such as Michael reac- tion, aldo reaction, Strecker reaction and carbometalation, cycloadditions, reduction reactions, cyclization, rearrangement reactions such as Ferrier rearrangement, Fries rearrangement, the sliding cyclohexane rearrangement, Beckman rear- rangement and the rearrangement of alkoxybenzyl allyl ethers into aldehydes, the formation and cleavage of common pro- tecting groups such as carbonyl compounds, carboxylic acids, amino groups and hydroxy groups, were reviewed. The use zirconium compounds including ZrCl4, ZrOCl2·8H2O, Zr(SO4)2·4H2O and Zr(HSO4)4, generally, allows the reaction to be carried out under mild conditions and affords the corresponding products in excellent yields with high regio-, chemo- and stereo-selectivity.
41 citations
TL;DR: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature.
29 citations
TL;DR: In this paper, the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles was presented, and the use of FeCl3 makes this method simple, convenient and cost-effective.
15 citations
TL;DR: The present reaction was shown to proceed under kinetic control to give approximately 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate.
14 citations
TL;DR: In this paper, the synthesis of d -myo-inositol 1,4,5-trisphosphate (InsP3) from methyl α-d -glucopyranose, via a type 2 Ferrier rearrangement is reported.
Abstract: The synthesis of d -myo-inositol 1,4,5-trisphosphate (InsP3) from methyl α- d -glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP3 derivatives. Biological evaluation of the synthetic InsP3 demonstrates that this compound evokes selective Ca2+ release via activation of InsP3 receptors.
9 citations
TL;DR: A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well.
7 citations
TL;DR: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity as discussed by the authors.
Abstract: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.
5 citations
TL;DR: In this paper, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed, using ZnCl2 impregnated on activated alumina.
Abstract: An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl- d -glucal to 2,3-unsaturated-O-glycosides with high α-selectivity.
TL;DR: In this paper, the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles was presented, and the use of FeCl3 makes this method simple, convenient and cost-effective.
Abstract: Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl3 under mild reaction conditions to provide C-glycosyl amides in good yields with high α-selectivity. The use of FeCl3 makes this method simple, convenient and cost-effective. This is the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles.
TL;DR: The use of zirconium compounds as a promoter and catalyst for many important organic reactions including addition reactions such as Michael reac- tion, aldo reaction, Strecker reaction and carbometalation was reviewed in this article.
Abstract: From a viewpoint of synthetic organic chemistry, the recent developments and applications of zirconium com- pounds as promoter and catalyst for many important organic reactions including addition reactions such as Michael reac- tion, aldo reaction, Strecker reaction and carbometalation, cycloadditions, reduction reactions, cyclization, rearrangement reactions such as Ferrier rearrangement, Fries rearrangement, the sliding cyclohexane rearrangement, Beckman rear- rangement and the rearrangement of alkoxybenzyl allyl ethers into aldehydes, the formation and cleavage of common pro- tecting groups such as carbonyl compounds, carboxylic acids, amino groups and hydroxy groups, were reviewed. The use zirconium compounds including ZrCl4, ZrOCl2·8H2O, Zr(SO4)2·4H2O and Zr(HSO4)4, generally, allows the reaction to be carried out under mild conditions and affords the corresponding products in excellent yields with high regio-, chemo- and stereo-selectivity.
TL;DR: In this paper, a rearrangement of anilides is proposed for the purpose of reducing nitroarenes in the reduction of nitro-arenes. But no abstract is given.
Abstract: This article has no abstract.
Keywords:
rearrangement of anilides;
aldol reaction;
chlorination of alcohols;
reduction of nitroarenes;
dithioacetalization;
michael reactions;
carbonyl regeneration;
episulfides;
diels–alder reactions;
allylations;
reformatsky-type reactions and reductions;
cyanohydrins;
beckmann rearrangement;
sulfonylation;
halogen exchange;
ferrier rearrangement;
heterocycles;
reductive etherification;
hydroarylation;
acylation and chlorosulfinylation;
α-aminonitriles;
1,2-diamines;
3,3-diarylpropenes;
substitutions;
4-methylcoumarins;
condensation;
cycloisomerization
TL;DR: In this paper, the addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst.
Abstract: The addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave sulfinate esters as products by reaction at oxygen rather than at sulfur. The sulfinate esters were obtained as mixtures of stereoisomers at the stereogenic sulfur atom. Trapping of the sulfinates with carboxylate nucleophiles was observed during attempted oxidation with MCPBA.
TL;DR: In this article, an anti-and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was achieved by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate.
Abstract: Highly anti- and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.
TL;DR: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature.
Abstract: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature. This methodology obviates the need for protecting and/or activating the C-3 hydroxyl group of glycals. The reaction works in equal ease with both 4,6-di-O-benzyl- d -glucal and 4,6-di-O-benzyl- d -galactal. The mildness of InCl3 makes this approach compatible for glycosyl acceptors with acid labile groups. The generality of the reaction has been demonstrated with a diversity of alcohols, phenols, and sugar nucleophiles.