253317-50-9Relevant academic research and scientific papers
Enantioselective Diels-Alder reactions catalyzed by chiral magnesium Lewis acids prepared from hydroxysulfoxides
Ordonez,Guerrero-De La Rosa,Labastida,Llera
, p. 2675 - 2686 (2007/10/03)
Enantioselective Diels-Alder reactions were conducted successfully using chiral magnesium complexes prepared from magnesium iodide and chiral hydroxysulfoxides derived from (R)- and (S)-methyl 1-naphthyl sulfoxide. Convenient methods for the preparation o
Atropisomer-selective ligand-coupling reactions of sulfoxides. X-Ray molecular and crystal structures for 2-(thiophen-3-yl>amino)-2-methylpropan-1-ol, 2-(2-hydroxy-1,1-dimethylethyl)-2,3-dihydronaphthoisothiazol-3-one and (R)-(+)-2-bromo-1-(tert...
Baker, Robert W.,Hockless, David C. R.,Pocock, Geoffrey R.,Sargent, Melvyn V.,Skelton, Brian W.,et al.
, p. 2615 - 2630 (2007/10/02)
1-(Alkyl- or aryl-sulfinyl)naphthalenes activated by electron-withdrawing substituents at the 2-position undergo substitution reactions on treatment with Grignard reagents.Evidence suggesting that these transformations proceed through ligand-coupling reactions of ?-sulfuranes is presented.The ligand-coupling reaction of homochiral sulfoxides with 1-naphthylmagnesium bromide furnishes atropisomeric 1,1'-binaphthyls in 60-95percent ee.Single-crystal X-ray structure determinations have been carried out on 2-(thiophen-3-yl>amino)-2-methylpropan-1-ol 18 and 2-(2-hydroxy-1,1-dimethylethyl)-2,3-dihydronaphthoisothiazol-3-one 22, compounds formed through intramolecular nucleophilic and electrophilic attack, respectively, on a neighbouring oxazoline group.The absolute configuration of (R)-(+)-1-(tert-butylsulfinyl)naphthalene 27 was determined by a single-crystal X-ray study of the 2-bromo-derivative 28.
Asymmetric Induction during Organometallic Conjugate Addition to Enantiomerically Pure 2-(Arylsulfinyl)-2-cyclopentenones
Posner, Gary H.,Mallamo, John P.,Hulce, Martin,Frye, Leah L.
, p. 4180 - 4185 (2007/10/02)
Virtually complete asymmetric induction is achieved during methyl-, vinyl- and naphthylmetallic conjugate addition to enantiomerically pure (S)-(+)-2-(p-tolylsulfinyl)-2-cyclopentenone ((S)-(+)-1). (R)-3-Methylcyclopentanone is obtained when the enone sul
