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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 22
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Synthetic Communications Reviews

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

, , , , &
Pages 2859-2865 | Received 17 Jun 2018, Published online: 10 Nov 2018
 

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

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].

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