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Chirality Exchange from sp3 Central Chirality to Axial Chirality:  Benzannulation of Optically Active Diaryl-2,2-dichlorocyclopropylmethanols to Axially Chiral α-Arylnaphthalenes

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posted on 05.05.2004, 00:00 by Yoshinori Nishii, Kazunori Wakasugi, Keisuke Koga, Yoo Tanabe
Chirality exchange benzannulation of optically active (1S)-aryl(aryl‘)-2,2-dichlorocyclopropylmethanols (>99% ee) using TiCl4 successfully proceeded to give axially chiral (M)-α-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.