Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral alpha-arylnaphthalenes.
Chirality exchange benzannulation of optically active (1S)-aryl(aryl')-2,2-dichlorocyclopropylmethanols (>99% ee) using TiCl4 successfully proceeded to give axially chiral (M)-alpha-arylnaphthalenes with excellent levels of stereo induction (>99% ee). This unique transformation involves the single-step chirality exchange from sp3 central chirality to axial chirality, that is, a type of excellent memory effect.
Nishii
Yoshinori
Y
Department of Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan. nishii@giptc.shinshu-u.ac.jjp
Wakasugi
Kazunori
K
Koga
Keisuke
K
Tanabe
Yoo
Y