153583-26-7Relevant academic research and scientific papers
Directed metalation/ligand coupling approach to the enantioselective synthesis of 1,1'-binaphthyls
Baker,Pocock,Sargent,Twiss
, p. 2423 - 2426 (1993)
Introduction of a 2-isopropoxycarbonyl or 2-N,N-dimethylcarbamoyl group into homochiral 1-p-tolyl- or 1-t-butyl-sulfinylnaphthalenes, via directed metalation reaction, followed by ligand coupling reaction with 1-naphthylmagnesium bromide, furnished atropisomeric 1,1'-binaphthyls in 82-95% enantiomeric excess (e.e.).
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.
