153683-84-2Relevant academic research and scientific papers
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.
Atropisomer-selective 1,1-Binaphthyl Synthesis via Chirality Transfer from Sulfur
Baker, Robert W.,Pocock, Geoffrey R.,Sargent, Melvyn V.
, p. 1489 - 1491 (2007/10/02)
4,5-Dihydro-2-(1-alkyl- or 1-aryl-sulfinylnaphthalen-2-yl)-4,4-dimethyloxazoles 3-6 undergo substitution reactions on treatment with Grignard reagents; the optically active sulfoxide 14 on treatment with 1-naphthylmagnesium bromide furnished the 1,1-binap
