ATROPISOMER-SELECTIVE 1,1'-BINAPHTHYL SYNTHESIS VIA CHIRALITY TRANSFER FROM SULFUR

Authors
BAKER RW SARGENT MV
Citation
Rw. Baker et Mv. Sargent, ATROPISOMER-SELECTIVE 1,1'-BINAPHTHYL SYNTHESIS VIA CHIRALITY TRANSFER FROM SULFUR, Pure and applied chemistry, 66(10-11), 1994, pp. 2143-2150
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Pure and applied chemistry → ACNP
ISSN journal
00334545
Volume
66
Issue
10-11
Year of publication
1994
Pages
2143 - 2150
Database
ISI
SICI code
0033-4545(1994)66:10-11<2143:A1SVCT>2.0.ZU;2-K
Abstract
1-(Alkyl- or aryl-sulfinyl)naphthalenes activated by electron-withdraw ing substituents at the 2-position undergo substitution reactions on t reatment with Grignard reagents. Evidence suggesting that this transfo rmation proceeds through a ligand coupling reaction of sigma-sulfurane s is discussed. The ligand coupling reaction of homochiral sulfoxides with 1-naphthylmagnesium bromide furnishes atropisomeric 1,1'-binaphth yls in 60-95% e.e.