2080-62-8Relevant academic research and scientific papers
A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization
Li, Sifan,Wang, Yu,Wu, Zibo,Shi, Weiliang,Lei, Yibo,Davies, Paul W.,Shu, Wei
, p. 7209 - 7214 (2021/09/14)
Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.
Au-catalyzed piperidine synthesis via tandem acyloxy migration/ intramolecular [3 + 2] cycloaddition of enynyl esters
Zheng, Huaiji,Huo, Xing,Zhao, Changgui,Jing, Peng,Yang, Juan,Fang, Bowen,She, Xuegong
, p. 6448 - 6451 (2012/02/03)
An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of
Desymmetrizations forming tetrasubstituted olefins using enantioselective olefin metathesis
Stenne, Brice,Timperio, Justin,Savoie, Jolaine,Dudding, Travis,Collins, Shawn K.
supporting information; experimental part, p. 2032 - 2035 (2010/07/03)
Figure presented Highly reactive chiral Ru-based catalysts possessing C1-symmetric N-heterocyclic carbene ligands adorned with one N-alkyl group and one N-aryl group were evaluated in asymmetric desymmetrizations to form cyclic products possess
A detailed investigation of the aza-prins reaction
Dobbs, Adrian P.,Guesne, Sebastien J. J.,Parker, Robert J.,Skidmore, John,Stephenson, Richard A.,Hursthouse, Mike B.
supporting information; experimental part, p. 1064 - 1080 (2010/06/13)
The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s). The Royal Society of Chemistry.
Poly(fluoroalkyl acrylate)-Bound Ruthenium Carbene Complex: A Fluorous and Recyclable Catalyst for Ring-Closing Olefin Metathesis
Yao, Qingwei,Zhang, Yiliang
, p. 74 - 75 (2007/10/03)
The synthesis of a fluorous olefin metathesis catalyst derived from the Grubbs second-generation ruthenium carbene complex is described. The air stable fluorous polymer-bound ruthenium carbene complex 1 shows high reactivity in effecting the ring-closing
Synthesis of N-heterocyclic diols by diastereoselective pinacol coupling reactions
Handa, Sandeep,Kachala, Manpreet S.,Lowe, Sarah R.
, p. 253 - 256 (2007/10/03)
A series of 5-8 membered N-heterocyclic diols have been prepared from acyclic dicarbonyls via diastereoselective pinacol reactions whereby cis- or trans-diol stereoselectivity is controlled by the choice of low-valent metal reagent used.
Synthesis of pyrrolidines and piperidines via palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides
Larock,Yang,Weinreb,Herr
, p. 4172 - 4178 (2007/10/02)
The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.
