Chirality Exchange from sp<sup>3</sup> Central Chirality to Axial Chirality: Benzannulation of Optically Active Diaryl-2,2-dichlorocyclopropylmethanols to Axially Chiral α-Arylnaphthalenes
Journal of the American Chemical SocietyPublished 13 April 2004
Yoshinori Nishii, Kazunori Wakasugi, Koga Keisuke, Yoo Tanabe
Citations87
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
Chirality exchange benzannulation of optically active (1S)-aryl(aryl')-2,2-dichlorocyclopropylmethanols using TiCl4 successfully proceeded to give axially chiral (M)-alpha-arylnaphthalenes with excellent levels of stereo induction.
Abstract
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.
Keywords
Chemistry
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