From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange.

Autor: Saito, Taichi, Shimizu, Yuka, Araki, Yusuke, Ohgami, Yoshino, Kitazawa, Yu, Nishii, Yoshinori
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Zdroj: European Journal of Organic Chemistry; 1/11/2022, Vol. 2022 Issue 1, p1-9, 9p
Abstrakt: Transformations of enantioenriched donor‐acceptor (D−A) cyclopropylcarbinols to enantioenriched 1‐arylnaphthalenes that bear an ortho‐substituent on a benzene ring provided a successful chirality‐exchange method with a high level of stereoinduction. A central chirality‐transfer step, i. e. a Lewis‐acid‐mediated ring‐opening cyclization of enantioenriched D‐A cyclopropylcarbinols (97 to >99 % ee), afforded 1‐aryl‐1,2‐dihydronaphthalenes with an ortho‐substituent (Me, Br, OMe, OBn, or OiPr) on the benzene ring with high enantioselectivity (97 to >99 % ee). The central‐to‐axial chirality‐exchange step, i. e. the dehydrogenation of the obtained enantioenriched 1‐aryl‐1,2‐dihydronaphthalenes using DDQ, furnished the axially chiral 1‐arylnaphthalenes with high enantioselectivity (90 to >99 % ee). Importantly, we developed a highly enantioselective synthesis of a 1‐arylnaphthalene with an ortho‐alkoxy group on the benzene ring. Moreover, we improved the chirality exchange to furnish a 1‐arylnaphthalene with an ortho‐alkoxy‐substituted benzene ring in high yield with high ee. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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