Issue 30, 2023

Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition

Abstract

Rhenium-catalyzed stereoselective transposition of allylic alcohols is reported. In the presence of 1 mol% of Re2O7, (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols.

Graphical abstract: Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Dec 2022
Accepted
01 Jul 2023
First published
06 Jul 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 8103-8108

Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition

J. Liu and M. Chen, Chem. Sci., 2023, 14, 8103 DOI: 10.1039/D2SC07059F

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