88335-63-1Relevant academic research and scientific papers
Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening
Luo, Lan,Yamamoto, Hisashi
supporting information, p. 10466 - 10470 (2015/11/10)
A virtually complete enantioselective synthesis of 3-amino-1,2-diols with three consecutive stereocenters was accomplished by a sequential cascade of two kinetic resolutions, which features a Sharpless or Hafnium-catalyzed asymmetric epoxidation and a subsequent W-catalyzed aminolysis. Enantiopure products with up to >99.9% ee and >99.9:0.1 dr were obtained and could serve as potential building blocks for pharmaceutical or biological significant molecules.
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
Asymmetric epoxidation via phase-transfer catalysis: Direct conversion of allylic alcohols into α,β-epoxyketones
Lygo, Barry,To, Daniel C. M.
, p. 2360 - 2361 (2007/10/03)
Studies into the use of a chiral phase-transfer catalyst in conjunction with sodium hypochlorite to effect the enantio-selective formation of α,β-epoxyketones from allylic alcohols are described.
Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: Synthesis of (S)-2-arylpropanoic acids
Carde, Lydia,Davies, D. Huw,Roberts, Stanley M.
, p. 2455 - 2463 (2007/10/03)
Poly-(D)-leucine-catalysed epoxidation of chalcone furnished epoxide (+)-6; treatment of this epoxide with trimethylaluminium followed by zinc borohydride reduction and oxidative cleavage furnished (S)-2-phenylpropanoic acid 11. In a complementary sequence epoxy ketones (-)-6 and 25 were converted into (S)-2-phenylpropanoic acid and (S)-fenoprofen 5 respectively by reduction with zinc borohydride, reaction with trimethylaluminium and oxidative cleavage. Similarly epoxy ketones (-)-6, 21 and 28 were treated with methylmagnesium iodide, trimethylaluminium and the resultant alcohols subjected to oxidative cleavage to afford (S)-2-phenylpropanoic acid (from the first two substrates) and (S)-naproxen 1.
Synthesis of novel C2-symmetric ligands based on (R,R)- and (S,S)- diphenyl-1,3-propanediol
Roos, Gregory H. P.,Donovan, A. Richard
, p. 991 - 1000 (2007/10/03)
A range of novel C2-symmetric dioxygen and dinitrogen ligands can readily be obtained through the interconversion of the parent 1,3-diphenyl- 1,3-propanediol enantiomers which are, in turn, accessed in good yields via a Sharpless asymmetric epoxidative resolution.
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.
Oxiranyllithium reagents: Generation from organotin precursors, addition to aldehydes and ketones, and dimerization to α,α′-dialkoxyolefins
Lohse, Peter,Loner, Helena,Acklin, Pierre,Sternfeld, Francine,Pfaltz, Andreas
, p. 615 - 618 (2007/10/02)
Oxiranyllithium compounds can be generated from organotin precursors by tin-lithium exchange with butyllithium in THF at -90°C. In the presence of TMEDA, they react with aldehydes and ketones to give epoxy alcohols in good yields. In the absence of TMEDA, they dimerize to α,α′-dialkoxyolefins.
A Novel Probe for Free Radicals featuring Epoxide Cleavage
Dickinson, Julia M.,Murphy, John A.,Patterson, Christopher W.,Wooster, Nicholas F.
, p. 1179 - 1184 (2007/10/02)
This paper describes the identification of carbon-carbon bond cleavage within a defined range of epoxides as being a reaction type which is specifically diagnostic of free radicals adjacent to the epoxide.The speed of the epoxide cleavage is greater than
