Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

ABSTRACT: Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with ?-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

SUBMITTER: Jarvis AN

PROVIDER: S-EPMC3678660 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Jarvis Ashley N AN McLaren Andrew B AB Osborn Helen M I HM Sweeney Joseph J

Beilstein journal of organic chemistry 20130502

Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity. ...[more]

PMID: 23766800

Similar Datasets

Stereospecific ring expansion of chiral vinyl aziridines.

Project description:In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

| S-EPMC3072884 | biostudies-literature

Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies.

Project description:The possibility to form new C-B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis.

| S-EPMC8659106 | biostudies-literature

Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines.

Project description:The ring opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparation of vicinal diamines. Our reaction is compatible with both disubstituted cis- and trans-aziridines; unsubstituted, N-alkyl, and N-aryl sulfamates engage effectively. In all cases examined, the cyclization reaction is perfectly regioselective and stereospecific. Once activated, the product oxathiazinane heterocycles can be ring opened with a diverse range of nucleophiles.

| S-EPMC10799289 | biostudies-literature

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions.

Project description:The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents.

| S-EPMC7418098 | biostudies-literature

Synthesis of ?-substituted tryptamines by regioselective ring opening of aziridines.

Project description:Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce ?-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

| S-EPMC4930112 | biostudies-literature

Alkylative Aziridine Ring-Opening Reactions.

Project description:In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening with external nucleophiles such as acetate and azide. Such alkylative aziridine ring opening provides an easy route for the synthesis of various N-alkylated amine-containing molecules with concomitant introduction of an external nucleophile at either its α- or β-position.

| S-EPMC8003214 | biostudies-literature

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with ?-Keto Esters

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with ?-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7116117 | biostudies-literature

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with β-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7508174 | biostudies-literature

Ring-opening and ring-expansion reactions of carborane-fused borirane.

Project description:Though the reaction chemistry of three-membered ring molecules such as cyclopropanes and their heteroatom-containing analogues has been extensively studied, the chemical properties of their boron analogues, boriranes, are little known thus far. This work describes the diverse reactivity patterns of carborane-fused borirane 2. This borirane engages in ring-opening reactions with different types of Lewis acids, such as BBr3, GeCl2, GaCl3, BH3(SMe2) and HBpin, affording a series of ring-opening products, in which M-X or B-H bonds add across the B-C(cage) bond of the three-membered ring in 2. On the other hand, borirane 2 can undergo ring-expansion reactions with unsaturated molecules such as PhCHO, CO2 and PhCN to give ring-expansion products, five-membered boracycles, via a concerted reaction mechanism as supported by DFT calculations. The results of this work not only enrich the reaction chemistry of boriranes, but also offer new routes to boron-containing compounds and heterocycles.

| S-EPMC8513813 | biostudies-literature

Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening.

Project description:We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well.

| S-EPMC10631200 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data