133371-96-7Relevant articles and documents
Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions
Babij, Nicholas R.,Boothe, Jordan R.,McKenna, Grace M.,Fornwald, Ryan M.,Wolfe, John P.
, p. 4228 - 4243 (2019/05/04)
The synthesis of bicyclic ureas and sulfamides via palladium-catalyzed alkene carboamination reactions between aryl/alkenyl halides/triflates and alkenes bearing pendant cyclic sulfamides and ureas is described. The substrates for these reactions are gene
A general, enantioselective synthesis of 1-azabicyclo[m.n.0]alkane ring systems
Senter, Timothy J.,Schulte, Michael L.,Konkol, Leah C.,Wadzinski, Tyler E.,Lindsley, Craig W.
, p. 1645 - 1648 (2013/04/10)
In this Letter, we describe a novel approach for the general and enantioselective synthesis of a diverse array of small to large 1-azabicyclo[m.n.0]alkyl ring systems with an embedded olefin handle for further functionalization. The stereochemistry is established via a highly diastereoselective indium-mediated allylation of an Ellman sulfinimine in greater than 9:1 dr, which is readily separable by column chromatography to afford a single diastereomer. This methodology allows for the rapid preparation of 1-azabicyclo[m.n.0]alkane ring systems that are not readily accessible through any other chemistry in excellent overall yields and, for many systems, the only enantioselective preparation reported to date.
Enantiopure 2-piperidylacetaldehyde as a useful building block in the diversity-oriented synthesis of polycyclic piperidine derivatives
Borsini, Elena,Broggini, Gianluigi,Colombo, Francesco,Khansaa, Maisaa,Fasana, Andrea,Galli, Simona,Passarella, Daniele,Riva, Elena,Riva, Sergio
experimental part, p. 264 - 269 (2011/05/11)
Novel, simple, and convenient strategies for diversely functionalized piperidine derivatives have been developed by using different metal catalyzed reactions starting from enantiopure (R)- and (S)-2-piperidylacetaldehyde.
Regioselective synthesis of azetidines or pyrrolidines by selenium-induced cyclization of secondary homoallylic amines
Franck, Xavier,Leleu, Stéphane,Outurquin, Francis
scheme or table, p. 4437 - 4440 (2010/09/20)
Azetidines or pyrrolidines can be regioselectively obtained by selenocyclization of homoallylic amines, according to the double bond substitution.
Preparation of enantiopure substituted piperidines containing 2-alkene or 2-alkyne Chains: Application to total syntheses of natural quinolizidine- alkaloids
Cheng, Guolin,Wang, Xinyan,Su, Deyong,Liu, Hui,Liu, Fei,Hu, Yuefei
supporting information; experimental part, p. 1911 - 1916 (2010/06/15)
"Chemical Equation Presented" A general method, for the preparation of enantiopure 2-alkene- or 2-alkyne-containing chain substituted piperidines was established by using nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead, of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within a few hours. To demonstrate the efficiency of the method and the versatility of the product, total, syntheses of natural alkaloids (+)-pelletierine((-)-lasubine II, and (-)-cermizine C were achieved by using (S)-2-allyl-N-Bocpiperidine as a versatile building block.
Stereocontrol in N-directed hydroboration: Synthesis of amino alcohols related to the piperidine alkaloids
Wang, Guoqiang,Vedejs, Edwin
scheme or table, p. 1059 - 1061 (2009/08/15)
Treatment of 2-(2'-alkenyl)-piperidine boranes with iodine or triflic acid induces internal hydroboration with high regiocontrol, even with a terminal alkene (R H). Good stereocontrol is possible for the N-benzyl substrates. Comparisons with acyclic model
Studies toward labeling cytisine with [11C]phosgene: Rapid synthesis of a δ-lactam involving a new chemoselective lithiation-annulation method
Rouden, Jacques,Seitz, Thomas,Lemoucheux, Laurent,Lasne, Marie-Claire
, p. 3787 - 3793 (2007/10/03)
With the aim of the radiolabeling of cytisine, a potent agonist of nicotinic receptors, with [11C]-phosgene, the rapid synthesis of a lactam model of our target has been studied. The key step of the δ-lactam formation is a new chemoselective lithiation-annulation method, under high dilution, of a suitable piperidinylcarbamoyl chloride. This precursor was obtained from (2-hydroxyethyl)-piperidine in a linear synthetic sequence involving a Corey-Fuchs olefination of the corresponding aldehyde, followed by a selective reduction, using a diimide equivalent, of an iodoalkyne into a (Z)-iodopropene piperidine. This alkene served as main precursor to study the cyclization according to several procedures using phosgene as the required carbonylating reagent.
Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)-and -(prop-2-ynyl)-piperidines
Ikeda, Masazumi,Kugo, Yasuhiro,Sato, Tatsunori
, p. 1819 - 1824 (2007/10/03)
Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[3.2.1]octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34). 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo-[3.2.1]octane 16 (75% as a diastereomeric mixture), along with the pyrido[2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%). 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.
A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine, (-)-pelletierine, (+)-δ-coniceine, and (+)-epidihydropinidine
Takahata, Hiroki,Kubota, Minoru,Takahashi, Seiki,Momose, Takefumi
, p. 3047 - 3054 (2007/10/03)
A new asymmetric route to 2-substituted piperidines involving the Sharpless asymmetric dihydroxylation (AD) of 5-hexenylazide 1 and an intramolecular aminocyclization as crucial steps and its application to the asymmetric synthesis of four piperidine alkaloids, (+)-coniine 2, (-)-pelletierine 3, (+)-δ-coniceine 4, aND (+)-epidihydropinidine 5 is presented.
On the Stereoselectivity of Nitrone Addition to α-Diphenylphosphinoylalkenes
Armstrong, Susan K.,Collington, Eric W.,Stonehouse, Jon,Warren, Stuart
, p. 2825 - 2832 (2007/10/02)
The title reaction was investigated for both achiral and α-chiral alkenes 1-3, and for cyclic and acyclic nitrones 4 and 8.In each case, addition to allyldiphenylphosphine oxide 1 gave a single isoxazolidine product.The configurations of these isoxazolidi
