26553-43-5Relevant articles and documents
Enantioselective one-pot catalytic synthesis of 4,5-epoxy-3-alkanols and 1-Phenyl-2,3-epoxy-1-alkanols from α,β-unsaturated aldehydes
Infante, Rebeca,Hernandez, Yulan,Nieto, Javier,Andres, Celia
supporting information, p. 4863 - 4869 (2013/08/23)
Conformationally restricted perhydrobenzoxazines have been demonstrated to be good chiral ligands for one-pot asymmetric ethylation/epoxidation, and the unprecedented arylation/epoxidation of trisubstituted α,β-unsaturated aldehydes. The scope of the reaction has been studied and a wide set of substrates with allylic strain of different nature has been explored, obtaining good or total diastereoselectivities in all cases. The enantiocontrol was good or high for the ethylation/epoxidation reaction, whereas it remained at moderate or good levels for the arylation/epoxidation. The reaction is general for trisubstituted enals, and alkylic and aromatic substituents are tolerated at both the α- and β-position of the unsaturated aldehyde; however, disubstituted enals remain challenging substrates. When the one-pot and two-pot protocols were compared, no significant differences concerning the stereocontrol were found, so the advantages of the one-pot procedure are clear. Copyright
Applications of free and resin-bound novel (trifluoromethyl)dioxiranes
Boehlow, Todd R.,Buxton, P. Christopher,Grocock, Estella L.,Marples, Brian A.,Waddington, Victoria L.
, p. 1839 - 1842 (2007/10/03)
Recyclable resin-bound and other trifluoromethyl aryl ketones are efficient catalysts for oxone mediated epoxidations.
Chemo- and stereoselective reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate
Ravikumar,Chandrasekaran, Srinivasan
, p. 9137 - 9142 (2007/10/03)
Reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate in dichloromethane under mild conditions (-78°→20°C) provides anti- (or erythro-) α,β-epoxy alcohols in high yields with high degree of chemo- and stereoselectivity.
