663604-97-5Relevant academic research and scientific papers
Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes
Verendel, J. Johan,Li, Jia-Qi,Quan, Xu,Peters, Byron,Zhou, Taigang,Gautun, Odd R.,Govender, Thavendran,Andersson, Pher G.
supporting information; scheme or table, p. 6507 - 6513 (2012/06/29)
Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. Copyright
Ring size-selective ring-closing olefin metathesis: Taking advantage of the deleterious effect of ethylene gas
Yoshida, Kazuhiro,Kano, Yuto,Takahashi, Hidetoshi,Yanagisawa, Akira
supporting information; experimental part, p. 1229 - 1233 (2011/07/08)
The deleterious effect of ethylene gas on the ring-closing olefin metathesis (RCM) for the formation of 5- to 8-membered rings was investigated. Significant rate differences caused by ethylene gas were observed among the different ring-size formation reac
Highly flexible synthesis of chiral azacycles via iridium-catalyzed hydrogenation
Verendel, J. Johan,Zhou, Taigang,Li, Jia-Qi,Paptchikhine, Alexander,Lebedev, Oleg,Andersson, Pher G.
supporting information; experimental part, p. 8880 - 8881 (2010/08/22)
A range of saturated chiral azacycles has been prepared in high yield and with high selectivity from simple starting materials. A modular approach with ring-closing metathesis as a key step was used to produce a number of five-, six-, and seven-membered c
Regioselective palladium-catalyzed formate reduction of N-heterocyclic allylic acetates
Cheng, Hsiu-Yi,Sun, Chong-Si,Hou, Duen-Ren
, p. 2674 - 2677 (2007/10/03)
The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethyl
N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: A comparative study in olefin metathesis
Clavier, Herve,Nolan, Steven P.
, p. 8029 - 8036 (2008/03/14)
Kinetic studies on ring-closing metathesis of unhindered and hindered substrates using phosphine and N-heterocyclic carbene (NHC)-containing ruthenium-indenylidene complexes (first and second generation precatalysts, respectively) have been carried out. T
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.
