Synthesis Of α-Amino Ketones Research Articles

Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines: synthesis of α-amino ketones

Herein we present a diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines catalyzed by a Rh(i) catalyst.

NHC-Catalyzed Aza-Benzoin Condensation of N,N'-Dipyridin-2-yl Aminals with Aldehydes.

α-Amino ketones are useful compounds because of their synthetic utility and bioactivities. After observing the ability of N,N'-dipyridin-2-yl aminals to form imines in situ, the synthesis of α-amino ketones using N,N'-dipyridin-2-yl aminals was proposed. Through the NHC-catalyzed aza-benzoin reaction between aromatic/aliphatic aldehydes and N,N'-dipyridin-2-yl aminals, α-amino ketones, including aromatic, heterocyclic, and aliphatic versions, were synthesized with yields up to 99%. A direct route toward N-Boc-protected α-amino ketones from N,N,N'-tris-Boc aminals was also discovered, yielding the desired N-Boc-protected α-amino ketones in yields up to 73%.

Recent advances in the synthesis of α-amino ketones.

Due to the importance of the amino ketone motif in synthetic and medicinal chemistry, the number of protocols developed in recent years has considerably increased. This review serves to collate and critically evaluate novel methodologies published since 2011 towards this high value synthon. The chapters are divided by the requisite functionality in the starting material, and an emphasis is placed on discussing functional group compatibility and resultant product substitution patterns. Throughout, applications to medicinal targets are highlighted and mechanistic details are presented, and we further provide a short outlook for future development and emerging potential within this area.

Enantioselective Synthesis of α-Amino Ketones by Asymmetric Counteranion-Directed Catalysis

Enantioselective Synthesis of α-Amino Ketones by Asymmetric Counteranion-Directed Catalysis

The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Brønsted Acids

An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.

Synthesis of α-Amino Ketones by Rhodium-Catalyzed Hydrogenation

Synthesis of α-Amino Ketones by Rhodium-Catalyzed Hydrogenation

One-pot, two-step conversion of alkynes to α-amino (α,α-diamino) ketones with a DMF-activated N-bromoimide strategy

A simple, one-pot, two-step cascade reaction for the synthesis of α-amino ketones has been developed.

Synthesis of α-Amino Ketones via Aminocyanation of Cyclic Enones

Synthesis of α-Amino Ketones via Aminocyanation of Cyclic Enones

Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles

N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

OsO4 — Catalyzed Synthesis of α-Amino Ketones: Improvement of Yield and Enantioselectivity.

OsO4 — Catalyzed Synthesis of α-Amino Ketones: Improvement of Yield and Enantioselectivity.

Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsily)amide. Ramberg-Bäcklund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.

α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. III. A Novel Synthesis of α-Amino Ketones and α-Amino Aldehydes by Aminolysis of α,β-Epoxy Sulfoxides

Abstract Aminolysis of α,β-epoxy sulfoxides, easily prepared from 1-chloroalkyl phenyl sulfoxides or chloromethyl phenyl sulfoxide and carbonyl compounds, with alkyl- or arylamines afforded α-amino ketones or α-amino aldehydes in good yields. Treatment of thus obtained α-arylamino ketones with weak Lewis acid led to 2,3-disubstituted indoles.

Synthesis of α-aminoketones via selective reduction of acyl cyanides

Reduction of acyl cyanides with zinc in acetic acid in the presence of excess acetic anhydride leads to N-acetyl-α-aminoketones in good yields. An efficient three-step synthesis of 5-aminolevulinic acid by this method is described.

Adducts of α-Lactams and a Dihydro-1,3-Oxazine: A Convenient Synthesis of α-Amino Ketones

Abstract The reaction of α-lactams (1a–1d) with tert-butyllithium at room temperature to yield α-hydroxy imines (5ax–5dx) was reported by us as the first example of a reaction between an α-lactam and an organolithium reagent.1 Subsequent investigation revealed that α-amino ketones (4ax–4dx) could be isolated from the reaction mixtures at lower temperatures under very carefully controlled conditions that prevent the rearrangement of 2 and 3.2 In fact, a variety of α-amino ketones were synthesized in this fashion,3 a result that was confirmed later by Baumgarten and co-workers.4 As part of a broader study of the reactions of a-lactams with organometallic reagents, we investigated the reactions of α-lactams with the lithium salt of 2,4,4,6-tetramethyl-5,6-dihydro-4H1,3-oxazine (6), a reagent that has been extensively used by Meyers5 for the synthesis of aldehydes. Although these reactions did not lead to aldehydes under the conditions described by Meyers, we did find them to be convenient routes to α-amino k...

A New Synthesis ofN-Substituted α-Amino Ketones

Abstract α-Amino ketones are valuable intermediates in the synthesis of a variety of substances, especially that of heterocyclic compounds, and their preparation and reactions continue to attract attention.1 Often, these compounds are prepared from the corresponding ketones or their α-bromo derivatives, but such syntheses may involve interfering side reactions and consequent difficulties in the isolation of the product.2 We now report a new synthesis of α-amino ketones which is based on a highly selective cleavage of α-lactams with organolithium compounds. This reaction is in sharp contrast to that of α-lactams with alkylmagnesium halides, which is claimed to effect an insertion-type alkylation of the acyl groups,3 although this claim has not been substantiated.4

Reactions of Amines. XI. Synthesis of α-Amino Ketones from Ketimines1,2

Reactions of Amines. XI. Synthesis of α-Amino Ketones from Ketimines^1,2

REACTIONS OF AMINES. VI. SYNTHESIS OF α-AMINO KETONES AND ACIDS FROM IMINO DERIVATIVES1,2

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTREACTIONS OF AMINES. VI. SYNTHESIS OF α-AMINO KETONES AND ACIDS FROM IMINO DERIVATIVES1,2Henry E. Baumgarten, Jerald E. Dirks, James M. Petersen, and Donald C. WolfCite this: J. Am. Chem. Soc. 1960, 82, 16, 4422–4423Publication Date (Print):August 1, 1960Publication History Published online1 May 2002Published inissue 1 August 1960https://doi.org/10.1021/ja01501a071RIGHTS & PERMISSIONSArticle Views232Altmetric-Citations7LEARN 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 (285 KB) Get e-Alerts Get e-Alerts