A new synthetic route for the synthesis of enantioenriched 1,2,3,4-tetrahydronaphthalene-derived 1,3-diols

Abstract

In this report, we presented a new approach to access a (1,3-butadiene-2-yl)carbinol, (1R,2R)- and (1S,2S)-1-(hydroxymethyl)-1-vinyl-1,2,3,4-tetrahydronaphthalene-2-ols. Starting from commercially available 1,4-diol-2-butyne, a six-step synthesis involving dibromination, Zn-mediated addition reaction of phenylpropyl aldehyde, epoxidation, epoxy–arene cyclization, and resolution with D(+)-Camphor afforded the title compounds.

Graphical Abstract

Keywords:

• Asymmetric synthesis
• 1,3-diene
• 1,3-diol
• oxetane

Additional information

Funding

We gratefully thank the financial support of this investigation by the National Natural Science Foundation of China [21573169, 21772151], Natural Science Foundation of Hubei Province [2018CFA084], and Wuhan Morning Light Plan of Youth Science and Technology [2017050304010314].