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

This article has now been updated. Please use the final version.

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

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Keywords: axially chiral enolate, asymmetric synthesis, chiral C-O axis, dihydrobenzofuran, conjugate addition, restricted bond rotation

JOURNAL FREE ACCESS Advance online publication

Article ID: c16-00272

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

The final version of this article is now available: Vol. 64 (2016), No. 7 pp. 899-906

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Abstract

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% ee.

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