Electrocyclization ofArylvinyl Oxetane/1,3-Diol toSubstituted Indenyl Acetaldehyde via Indene–Ethanol, Oxepine,and a 1,6-Hydride Shift

We intended to realize aryl vinyl oxetane as a 4π-electrocyclization precursor to access indene ethanol. Interestingly, we found that the readily accessible aryl vinyl 1,3-diol, an intermediate en route to the synthesis of oxetane, is an equally potential precursor for the anticipated cyclization. Moreover, aryl vinyl 1,3-diol/oxetane and indene ethanol readily reacted with the subsequently added (het)aromatic aldehydes, providing various indene oxepines/acetaldehydes. Additionally, indenyl aldehyde served as a synthetic handle for FGI, further expanding this protocol’s scope.

Publication Details

Journal
Figshare
Published
2025-02-12
DOI
https://doi.org/10.1021/acs.joc.4c03126.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Electrocyclization ofArylvinyl Oxetane/1,3-Diol toSubstituted Indenyl Acetaldehyde via Indene–Ethanol, Oxepine,and a 1,6-Hydride Shift

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Electrocyclization ofArylvinyl Oxetane/1,3-Diol toSubstituted Indenyl Acetaldehyde via Indene–Ethanol, Oxepine,and a 1,6-Hydride Shift

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Abstract

We intended to realize aryl vinyl oxetane as a 4π-electrocyclization precursor to access indene ethanol. Interestingly, we found that the readily accessible aryl vinyl 1,3-diol, an intermediate en route to the synthesis of oxetane, is an equally potential precursor for the anticipated cyclization. Moreover, aryl vinyl 1,3-diol/oxetane and indene ethanol readily reacted with the subsequently added (het)aromatic aldehydes, providing various indene oxepines/acetaldehydes. Additionally, indenyl aldehyde served as a synthetic handle for FGI, further expanding this protocol’s scope.

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Mycorrhizal Fungi and Plant Interactions
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Electrocyclization ofArylvinyl Oxetane/1,3-Diol toSubstituted Indenyl Acetaldehyde via Indene–Ethanol, Oxepine,and a 1,6-Hydride Shift · Figshare (2025) | TGRS Research Map | TGRS