129083-33-6Relevant academic research and scientific papers
Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis
Morrill, Christie,Grubbs, Robert H.
, p. 2842 - 2843 (2005)
Two reaction strategies are developed to promote the highly selective 1,3-isomerization of a variety of allylic alcohols using O3ReOSiPh3 as a catalyst. The first strategy utilizes substrates whose 1,3-regioisomer contains a conjugated alkene, which relies on thermodynamics to obtain high selectivity. The second strategy employs N,O-bis(trimethylsilyl)acetamide as an additive to selectively and irreversibly remove the product from the reaction equilibrium and works well for the isomerization of tertiary allylic alcohols into primary allylic alcohols containing trisubstituted alkene components. High stereoselectivity is also observed in the 1,3-isomerization of enantioenriched allylic alcohols. Copyright
Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes
Elbert, Bryony L.,Lim, Diane S. W.,Gudmundsson, Haraldur G.,O'Hanlon, Jack A.,Anderson, Edward A.
, p. 8594 - 8598 (2014/07/21)
Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
SELECTIVE REDUCTION OF ALKYNES TO CIS-ALKENES BY HYDROMETALLATION USING 6
Daeuble, John F.,McGettigan, Colleen,Stryker, Jeffrey M.
, p. 2397 - 2400 (2007/10/02)
Selective reduction of alkynes to the corresponding alkenes is reported using the stable, readily prepared copper(I) hydride reagent, 6.Terminal alkynes are reduced at room temperature, unactivated internal alkynes react only at elevated temperature.Disubstituted alkynes with propargyl activation are also reduced, giving cis-olefins selectively.Protection of propargylic alcohol functionality is unnecessary, although fragmentation is sometimes competitive in sterically hindered cases.A tertiary propargyl acetate gave displacement to the allene exclusively.
