Opening Of Aziridines Research Articles

Total synthesis of the putative structure of the marine metabolite trunkamide A

The structure assigned to trunkamide A, a cycloheptapeptide alkaloid isolated from the colonial ascidian Lissoclinum sp., was prepared via segment condensations and an efficient oxazoline-thiazoline interconversion. The novel reverse prenylated serine and threonine amino acid building blocks were obtained by Lewis acid assisted opening of aziridines. In light of this total synthesis, the structure of natural trunkamide A needs to be revised.

Nucleophilic ring opening of aziridines

This account of research work on nucleophilic ring opening (NRO) of aziridines (Az's) demonstrates the broad synthetic scope of this reaction, inclusive secondary reactions, and it discusses the special mechanistic fundamentals and details as well as mechanistic variants. Formation of a C–C bond by NRO is the red thread in this report. A central mechanistic aspect is the quality of the leaving group in Az bases, aziridinium ions and activated Az's (acyl, sulfonyl; double activation). Factors controlling the regioselectivity of NRO are dealt with as well as the influence of the nitrogen pyramid. Competing reactions include carbonyl attack (acylated Az's) and electron transfer with cases of pseudo-NRO (multistep radical paths).

ChemInform Abstract: Regioselective Nucleophilic Ring Opening of Epoxides and Aziridines Derived from Homoallylic Alcohols.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Design and synthesis of some new C2‐symmetric chiral disulfonamides from aminoacids and the application in diethyl zinc addition to benzaldehyde

AbstractNine C2‐symmetric chiral disulfonamides were designed and synthesized from L‐valine, L‐phenylalanine and L‐leucine respectively via one‐pot ring opening of aziridines. The application of these disulfonamides as catalyst in the addition of diethyl zinc to benzaldehyde in three reagent systems: Ligand‐Ti(OiPr)r‐Et2Zn; Ligand‐Ti(O'Pr)d‐HzO‐Et2Zn; Ligand‐Et2Zn was also described.

Regioselective nucleophilic ring opening of epoxides and aziridines derived from homoallylic alcohols

The regioselectivity of nucleophilic ring opening of some 3,4-epoxy and 3,4-aziridino alcohols has been studied. The nucleophiles chosen were complex hydrides (LiAlH 4, Red-Al and DIBAL) and Lipshutz- or Gilman-type organocuprate reagents. The C-4 substituent in the substrates was varied in order to study steric and electronic effects on the ring opening reactions. For alkyl substituents at C-4, most of the results can be explained on the basis of intramolecular delivery of the nucleophile to C-3 via a six-membered transition state, leading to 1,4-diols or 1,4-amino alcohol derivatives. In general, the epoxy alcohols gave poorer regioselectivity than the N-tosyl aziridino alcohols, for which selectivities of >95:5 were routinely obtained. The activating effect of a phenyl group at C-4 led to a switch in regiochemistry, with the 1,3-diol or 1,3-amino alcohol derivative as the major product.

ChemInform Abstract: Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Part 2. Synthesis and Ring‐Opening Reactions of Aziridines Derived from 5,6‐Dihydro‐2H‐pyran and of the Diastereoisomeric cis‐ and trans‐Aziridines Derived from 3‐(Benzyloxy) cyclohexene, 2‐(Benzyloxy)‐3,6‐dihydro‐, and 2‐(Benzyloxy)‐6‐methyl‐3, 6‐dihydro‐2H‐pyran.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Formation of Scalemic Aziridines via the Nucleophilic Opening of Aziridines.

ADVERTISEMENT RETURN TO ISSUEPREVNoteFormation of Scalemic Aziridines via the Nucleophilic Opening of AziridinesStephen C. Bergmeier and Punit P. SethView Author Information Division of Medicinal Chemistry, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210 Cite this: J. Org. Chem. 1997, 62, 8, 2671–2674Publication Date (Web):April 18, 1997Publication History Received10 December 1996Published online18 April 1997Published inissue 1 April 1997https://doi.org/10.1021/jo962307fCopyright © 1997 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views940Altmetric-Citations34LEARN 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 Read OnlinePDF (218 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Aziridines,Organic compounds,Organometallic reactions,Reagents,Ring opening reactions Get e-Alerts

ChemInform Abstract: Ytterbium Triflate Catalyzed Ring Opening of Aziridines with Amines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Regiochemical control of the ring opening of aziridines by means of chelating processes. 2. Synthesis and ring-opening reactions of aziridines derived from 5,6-dihydro-2 H-pyran and of the diastereoisomeric cis- and trans-aziridines derived from 3-(benzyloxy)cyclohexene, 2-(benzyloxy)-3,6-dihydro-, and 2-(benzyloxy)-6-methyl-3,6-dihydro-2 H-pyran

The regiochemical outcome of the ring opening of the activated and unactivated title aziridines was examined. In some cases a nice degree of regiocontrol can be obtained depending on the opening reaction conditions (standard, metal-assisted, or under acid-proton catalysis). The results have been rationalized by admitting the incursion, under appropriate reaction conditions, of chelated bidentate structures in which the metal or, in some cases, the proton is coordinated between the aziridine nitrogen and the O-heterofunctionality.

Total synthesis of ( ent)-korupensamine D

The first total synthesis of the enantiomer of the natural product, korupensamine D ( 16R), is described. The key steps include a highly efficient preparation of the enantiomerically pure primary amine 4 via the ring opening of aziridine 2 with an arylcuprate reagent and the development of a one-pot selective functionalization of a hindered secondary amine in the presence of phenolic hydroxyl groups (i.e., 8 to 9).

Ytterbium Triflate Catalyzed Ring Opening of Aziridines with Amines

Ytterbium Triflate Catalyzed Ring Opening of Aziridines with Amines

Interaction of N‐tert‐butylaziridine with π‐electron acceptors, 1. Zwitterion copolymerization with maleic anhydride

AbstractZwitterion copolymerization of N‐tert‐butylaziridine (TBA) with the weak π‐electron acceptor maleic anhydride (MA) was investigated. It was demonstrated that the reaction proceeds by opening of both aziridine and anhydride rings, and copoly(ester‐amide)s of different composition were prepared depending on the polymerization conditions. On the basis of a model reaction it was assumed that charge‐transfer interaction is a stage of the zwitterion mechanism. The structure and the composition of the products obtained were investigated.

ChemInform Abstract: SN2′ Ring Opening of Aziridines Bearing an α,β‐Unsaturated Ester Group with Organocopper Reagents. A New Stereoselective Synthetic Route to (E)‐Alkene Dipeptide Isosteres.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Synthesis and Ring-Opening Reactions of cis- and trans-Aziridines Derived from 4-(Benzyloxy)cyclohexene

Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Synthesis and Ring-Opening Reactions of cis- and trans-Aziridines Derived from 4-(Benzyloxy)cyclohexene

ChemInform Abstract: Ytterbium Triflate Catalyzed Ring Opening of Aziridines with Amines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

SN2′ Ring opening of aziridines bearing an α,β-unsaturated ester group with organocopper reagents. A new stereoselective synthetic route to (E)-alkene dipeptide isosteres

Regio- and stereo-selective synthesis of (E)-alkene dipeptide isosteres has been successfully achieved by exposing both (E)- and (Z)-N-(4-methylphenyl)sulfonyl-γ,δ-epimino-α,β-enoates to organocopper reagents at –78 °C for 30 min.

Ytterbium triflate catalyzed ring opening of aziridines with amines

Ring opening of aziridines with amines takes place readily in the presence of catalytic amount of ytterbium triflate, giving the corresponding 1, 2-diamines in good to high yields.

ChemInform Abstract: Naphthalene‐Catalyzed Reductive Opening of Aziridines with Lithium: A Direct Preparation of N‐Lithio‐2‐lithioalkylamines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ring Opening of Epoxides with Acetone Cyanohydrin Catalyzed by Lanthanoid(III) Alkoxides

Abstract Ring opening of epoxide and aziridine with acetone cyanohydrin is promoted by a catalytic amount of lanthanoid(III) alkoxide to provide β-hydroxy nitrile and β-amino nitrile, respectively.

Naphthalene-catalysed reductive opening of aziridines with lithium: A direct preparation of n-lithio-2-lithioalkylamines

The reductive opening of N-phenylaziridine ( 1) with an excess of lithium presence of a catalytic amount (5 molar %) of naphthalene at −78°C leads to the corresponding N-lithio-2-lithioethylamine ( 2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected product ( 3). The same process applied to N-cyclohexylaziridine fails. The reactions also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.