81758-22-7Relevant academic research and scientific papers
Modular Synthesis of Triazole-Based Chiral Iodoarenes for Enantioselective Spirocyclizations
Hempel, Christian,Maichle-M?ssmer, Caeciliea,Pericàs, Miquel A.,Nachtsheim, Boris J.
, p. 2931 - 2941 (2017/09/06)
A new triazole-based C1-symmetrical chiral iodoarene was synthesized in a highly modular route. Based on enzymatic kinetic resolution of an easily accessible propargylic alcohol both enantiomers were accessible in enantiopure form. By Huisgen-type azide-alkyne cycloaddtion a series of differently substituted iodoarenes was synthesized in high overall yields. Finally this novel iodoarene was successfully applied in the oxidative Kita cyclization of naphthol derivatives. Good yields and high ee values were obtained in the asymmetric spirocyclization via in situ generation of the hypervalent iodine species using mCPBA as the terminal oxidant. (Figure presented.).
Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives
Chen, Cuili,Chen, Xianxiao,Zhang, Xiaoxiang,Wang, Shifa,Rao, Weidong,Chan, Philip Wai Hong
supporting information, p. 4359 - 4368 (2017/12/26)
A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771. (Figure presented.).
Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction
Chinta, Bhavani Shankar,Baire, Beeraiah
, p. 10208 - 10217 (2015/11/03)
A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl-piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step.
First generation of the dienediyne portion of a dienediyne model of the neocarzinostatin chromophore by a McMurry reaction
Rucker, Mark,Brueckner, Reinhard
, p. 7353 - 7356 (2007/10/03)
The first 3→6 type ring-closing dienediyne synthesis by means of a McMurry reaction was realized by converting the ketoaldehyde 20 into the 6-/10-membered bicyclic dienediyne 22. Diastereoselective pinacol couplings 20→23 and 21→24 giving 6-/10-membered b
Tandem radical reactions of isonitriles with 2-pyridonyl and other aryl radicals: Scope and limitations, and a first generation synthesis of (±)-camptothecin
Curran, Dennis P.,Liu, Hui,Josien, Hubert,Ko, Sung-Bo
, p. 11385 - 11404 (2007/10/03)
Photolysis of N-propargyl-6-halo-2-pyridones and related aromatic halides in the presence of aryl isonitriles provides tetra- and penta-cyclic products in a single step by a sequence of radical addition to the isonitrile followed by two cyclizations. The scope and limitations of the process are described along with a first generation synthesis of racemic camptothecin.
