57716-80-0Relevant academic research and scientific papers
A phosphine-free iron complex-catalyzed synthesis of cycloalkanes: Via the borrowing hydrogen strategy
Bettoni, Léo,Gaillard, Sylvain,Renaud, Jean-Luc
, p. 12909 - 12912 (2020)
Herein we report a diaminocyclopentadienone iron tricarbonyl complex catalyzed synthesis of substituted cyclopentane, cyclohexane and cycloheptane compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary 1,n diols as alkylating reagents. Deuterium labeling experiments confirm that the diols were the hydride source in this cascade process. This journal is
Stereospecificite de l'addition de Michael d'enethiolates avec les enones acyliques
Kpegba, Kafui,Metzner, Patrick,Rakotonirina, Rose
, p. 2041 - 2056 (2007/10/02)
1,4-Addition reaction of lithiated dithioesters with acyclic β-substituted E enones affords diastereomeric 5-oxo-alkanedithioates.Anti configuration was assigned to yhe major diastereoisomer by chemical correlation.This stereochemistry depends on the configuration of the prochiral partners.The cis/trans ratio of intermediate enethiolates was analyzed by trapping experiments.Two cases of highly selective cis deprotonation of dithioesters were observed.Michael addition with E-enones (3-penten-2-one, chalcone) occurs with high stereospecificity : anti/syn product ratios are identical to the cis/trans enethiolate ratios.A pseudo-cyclic transition state is proposed with substituents of the enone C-C double bond occupying favorable equatorial positions.The 1,4-addition reaction is kineticaly controlled.In contrast to ester enolates, enethiolates allow the use of enones without the need of tertiobutyl or phenyl groups.The observed diastereoselectivity (ratio anti/syn up to 95:5) offers a new means of creation of two vicinal carbon substituted asymmetric centers by carbon-carbon bond formation in the acyclic series.Poor selectivities were however observed when using unsaturated diesters as acceptors.
