Hydride Reagents Research Articles

Asymmetric Reduction of Prochiral Ketones with Chiral Hydride Reagents Prepared from Lithium Aluminium Hydride and (S)-2-(N-Substituted aminomethyl)pyrrolidines

Abstract Asymmetric reduction of prochiral ketones with various hydride reagents prepared from lithium aluminium hydride and (S)-2-(N-substituted aminomethyl) pyrrolidines, derived easily by four steps from commercially available (S)-proline, yields optically active alcohols with 13–92% optical purity having the S-configuration.

ASYMMETRIC REDUCTION OF ACETOPHENONE WITH CHIRAL HYDRIDE REAGENT PREPARED FROM LITHIUM ALUMINIUM HYDRIDE AND (S)-2-(ANILINOMETHYL)PYRROLIDINE

Abstract (S)-2-(Anilinomethyl)pyrrolidine (1), new chiral diamine, is easily prepared by four steps starting from (S)-proline. Asymmetric reduction of acetophenone with chiral hydride reagent, prepared from (1) and lithium aluminium hydride, gives (S)-1-phenylethanol in 92% optical yield (93% yield).

Conformational control. An important factor in the stereoselective reduction of ketones by bulky hydride reagents

Conformational control. An important factor in the stereoselective reduction of ketones by bulky hydride reagents

Base-induced rearrangements of 3-(α-haloacyl)indoles : A convenient route to indole-3-acetic acids and tryptopholes

Base-induced reactions of 3-(α-haloacyl)indoles have been investigated. Rearrangement is a general reaction observed under the influence of various bases, e.g. hydroxide, hydride and Grignard reagent. Indole-3-acetic acids ( 20–32) are formed in fair yields when the reaction is performed with sodium hydroxide in 80% aqueous ethanol. The carbon monoxide evolved during the reaction appears to be eliminated from an intermediate cyclopropanone ( 33). Tryptopholes ( 53–55) are prepared in good yields by LiAlH 4-reduction of 3-(α-haloacyl)indoles.

Saline hydrides and superbases in organic reactions. VII. Potassium hydride, highly active new hydride reagent. Reactivity, applications, and techniques in organic and organometallic reactions

Saline hydrides and superbases in organic reactions. VII. Potassium hydride, highly active new hydride reagent. Reactivity, applications, and techniques in organic and organometallic reactions

Oxazolines. XI. Synthesis of functionalized aromatic and aliphatic acids. Useful protecting group for carboxylic acids against Grignard and hydride reagents

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxazolines. XI. Synthesis of functionalized aromatic and aliphatic acids. Useful protecting group for carboxylic acids against Grignard and hydride reagentsA. I. Meyers, Davis L. Temple, Dan Haidukewych, and Edward D. MihelichCite this: J. Org. Chem. 1974, 39, 18, 2787–2793Publication Date (Print):September 1, 1974Publication History Published online1 May 2002Published inissue 1 September 1974https://doi.org/10.1021/jo00932a024RIGHTS & PERMISSIONSArticle Views2834Altmetric-Citations128LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (947 KB) Get e-Alerts Get e-Alerts

Synthesis via oxazolines. VII. Asymmetric reduction of ketones with chiral hydride reagents

Synthesis via oxazolines. VII. Asymmetric reduction of ketones with chiral hydride reagents

Stereoselectivity in the reduction of aliphatic .alpha.-ketols with aluminum hydride reagents

Stereoselectivity in the reduction of aliphatic .alpha.-ketols with aluminum hydride reagents

Quinoline alkaloids. XV. Reactions of a quinoline isoprenyl epoxide with hydride reagents. Asymmetric synthesis and stereochemistry of lunacridine and related Lunasia alkaloids.

Reaction of (–)-3-(2,3-epoxy-3-methylbutyl)-2,4,8-trimethoxyquinoline, of known configuration, with diborane–lithium borohydride or with lithium aluminium hydride–aluminium chloride gave a secondary alcohol which was converted into (–)-lunacridine. The stereochemistry ofLunasiaalkaloids is discussed. Reductive displacement of 4-methoxy-groups in 2,4,8-trimethoxyquinoline derivatives occurs with lithium aluminium hydride. Rearrangement products obtained from the quinoline epoxide with mixed hydrides and with acid are described.

The surface hydroxyl population in bone mineral

Lithium aluminium hydride reagent has been employed in the determination of surface OH groups in bone mineral which may be described as an impure hydroxyapatite. The dehydrated sample is dropped into a diglyme solution of LiAlH4 and hydrogen gas evolution is measured. One mole of hydrogen is evolved by each mole of OH groups. The total surface is previously measured by the B.E.T. nitrogen adsorption method. Thus it is possible to compare the number of surface OH groups found per unit area with that estimated on the basis of the known crystal lattice. Less than fifty percent of the estimated number is found. Several possible explanations for the apparent discrepancy are offered. Perhaps the most compelling one is the suggestion of an actual deficiency of surface hydroxyl groups.

ANTINEOPLASTIC AGENTS: X. N-BIS(2-FLUOROETHYL)AMINES

Successive conversion of N-bis(2-hydroxyethyl)-p-toluenesulphonamide (Ib) to respective dimethanesulphonate and difluoro derivatives (IIa, IIIa, and IIIc) was found to provide a convenient route to N-bis(2-fluoroethyl)amine. Reaction of N-bis(2-methanesulphonyl-oxyethyl)-p-toluenesulphonamide (IIIa) with limited quantities of potassium fluoride, in several pro tic solvents, was shown to yield N-(p-toluenesulphonyl)morpholine (IV). Utility of N-bis(2-fluoroethyl)amine as a precursor of fluoro-nitrogen mustards was illustrated by synthesis of two N-bis(2-fluoroethyl)benzylamines (IXb and Xa). Application of an aluminum chloride – lithium aluminum hydride reagent for hydrogenolysis of carbon–fluorine bonds was also suggested.

The Determination of Complex Formation in Mixed Solvents by Gas Chromatography. The Tetrahydrofuran Complexes of Lithium Aluminum Hydride, Magnesium Bromide, and Several Grignard Reagents

The Determination of Complex Formation in Mixed Solvents by Gas Chromatography. The Tetrahydrofuran Complexes of Lithium Aluminum Hydride, Magnesium Bromide, and Several Grignard Reagents

Investigations on organo‐tin compounds. XII. The action of lithium aluminium hydride and grignard reagents on organo‐tin nitriles and esters

AbstractReactions of cyanoalkyl‐ and methoxycarbonylalkyl‐tin compounds with lithium aluminium hydride and Grignard reagents have been studied. Several new organo‐tin compounds containing hydroxyalkyl, aminoalkyl and ketoalkyl groups are described.

Nitrogen Analogs of Ketenes. III. Formation of Hydroperoxides and Vinylamines by Reaction with Lithium Aluminum Hydride and Organometallic Reagents1,2

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNitrogen Analogs of Ketenes. III. Formation of Hydroperoxides and Vinylamines by Reaction with Lithium Aluminum Hydride and Organometallic Reagents1,2Calvin L. Stevens and Robert J. GasserCite this: J. Am. Chem. Soc. 1957, 79, 22, 6057–6062Publication Date (Print):November 1, 1957Publication History Published online1 May 2002Published inissue 1 November 1957https://doi.org/10.1021/ja01579a058RIGHTS & PERMISSIONSArticle Views109Altmetric-Citations20LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (792 KB) Get e-Alerts Get e-Alerts

The Action of Lithium Aluminum Hydride and Organometallic Reagents on 4-Hydroxycoumarin1

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Action of Lithium Aluminum Hydride and Organometallic Reagents on 4-Hydroxycoumarin1Jeremiah P. Freeman and M. Frederick HawthorneCite this: J. Am. Chem. Soc. 1956, 78, 14, 3366–3369Publication Date (Print):July 1, 1956Publication History Published online1 May 2002Published inissue 1 July 1956https://doi.org/10.1021/ja01595a029RIGHTS & PERMISSIONSArticle Views157Altmetric-Citations9LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (509 KB) Get e-Alerts Get e-Alerts