127310-97-8Relevant academic research and scientific papers
The hydrogen bond directing effect in nitrile oxide cycloadditions to allylic substituted cyclopentenes
Cardarelli, Anna Maria,Fassardi, Vera,Memeo, Misal Giuseppe,Quadrelli, Paolo
, p. 2602 - 2613 (2017/04/10)
A quantitative evaluation of the H-bond directing effect on the stereoselectivity in the cycloaddition of nitrile oxides to 2-cyclopenten-1-ol and allylic cyclopentenyl amides is reported. In apolar solvents the H-bond directing effect promotes a high syn stereoselectivity while H-bond acceptor solvents divert the reactions to the anti face of the dipolarophile. Taft's β parameter gives a good description of the solvent effect on the H-bond directing effect. The persistence of some syn stereoselectivity even in good H-bond acceptor solvents points out the existence of some residual hydrogen bond direction. The syn stereoselectivity in the presence of M(II) salts was also investigated and the results discussed in the light of the potential application of these scaffolds in nucleoside synthesis.
HYDROGEN BOND DIRECTED NITRILE OXIDE CYCLOADDITION REACTIONS OF ALLYLIC 2o-AMIDES
Curran, Dennis P.,Gothe, Scott A.,Choi, Sung-Mo
, p. 1371 - 1395 (2007/10/02)
The ability of allylic and homoallylic 2o-amides to direct nitrile oxide cycloaddition reactions has been studied.For N-cyclopentenyl amides, good regio- and stereochemical control are observed and mechanistic studies suggest that hydrogen bond
Directed Nitrile Oxide Cycloaddition Reactions. The Use of Hydrogen Bonding To Direct Regio- and Stereochemistry in Nitrile Oxide Cycloadditions with Cyclopentenylamides
Curran, Dennis P.,Choi, Sung-Mo,Gothe, Scott A.,Lin, Fu-tyan
, p. 3710 - 3712 (2007/10/02)
2 deg amides derived from cyclopentenylamine direct the regio- and stereochemistry of cycloaddition reactions with benzonitrile oxide and 2,2-dimethylpropane nitrile oxide by hydrogen bonding.
