Asymmetric Synthesis of Multisubstituted Dihydrobenzofurans by Intramolecular Conjugate Addition of Short-Lived C–O Axially Chiral Enolates

Keisuke Tomohara; Koji Kasamatsu; Tomoyuki Yoshimura; Takumi Furuta; Takeo Kawabata

doi:10.1248/cpb.c16-00272

Special Collection of Papers: Regular Articles

Asymmetric Synthesis of Multisubstituted Dihydrobenzofurans by Intramolecular Conjugate Addition of Short-Lived C–O Axially Chiral Enolates

Keisuke Tomohara, Koji Kasamatsu, Tomoyuki Yoshimura, Takumi Furuta, Takeo Kawabata

著者情報

キーワード: axially chiral enolate, asymmetric synthesis, chiral C–O axis, dihydrobenzofuran, conjugate addition, restricted bond rotation

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2016 年 64 巻 7 号 p. 899-906

DOI https://doi.org/10.1248/cpb.c16-00272

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抄録

Enantioselective intramolecular conjugate addition reactions of short-lived C–O axially chiral enolates have been developed. The reactions proceeded with inversion of the configuration and provided dihydrobenzofurans with contiguous tetra- and trisubstituted carbon centers in up to 96% enantiomeric excess (ee).

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