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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.

SUBMITTER: Liu J 

PROVIDER: S-EPMC10395275 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Stereoselective syntheses of 2-methyl-1,3-diol acetals <i>via</i> Re-catalyzed [1,3]-allylic alcohol transposition.

Liu Jiaming J   Chen Ming M  

Chemical science 20230706 30

Rhenium-catalyzed stereoselective transposition of allylic alcohols is reported. In the presence of 1 mol% of Re<sub>2</sub>O<sub>7</sub>, (<i>E</i>)- or (<i>Z</i>)-δ-hydroxymethyl-<i>anti</i>-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-<i>syn</i>-diols with excellent diastereoselectivities. 1,3-<i>syn</i>-Diol acetals can also be synthesized from (<i>E</i>)-δ-hydroxymethyl-<i>syn</i>-homoallylic alcohols. ...[more]

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