Copper-Catalyzed\nCarbomagnesiation of 1‑Halocyclopropenes

We report a versatile copper-catalyzed carbomagnesiation\nreaction\nof poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning\nthe regioselectivity of the addition, we were able to access configurationally\nstable fully substituted cyclopropyl carbenoid intermediates. These\nintermediates were subsequently trapped with electrophiles to furnish\nstereodefined poly- and fully substituted halocyclopropyl esters.\nThe regioselectivity of the addition was found to be dependent on\nthe nature of the sp<sup>2</sup> substituents.

Publication Details

Journal
Figshare
Published
2024-10-17
DOI
https://doi.org/10.1021/acs.orglett.4c03507.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

Copper-Catalyzed\nCarbomagnesiation of 1‑Halocyclopropenes

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Cyclopropane Reaction Mechanisms
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Copper-Catalyzed\nCarbomagnesiation of 1‑Halocyclopropenes

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Abstract

We report a versatile copper-catalyzed carbomagnesiation\nreaction\nof poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning\nthe regioselectivity of the addition, we were able to access configurationally\nstable fully substituted cyclopropyl carbenoid intermediates. These\nintermediates were subsequently trapped with electrophiles to furnish\nstereodefined poly- and fully substituted halocyclopropyl esters.\nThe regioselectivity of the addition was found to be dependent on\nthe nature of the sp<sup>2</sup> substituents.

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Cyclopropane Reaction Mechanisms
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Copper-Catalyzed\nCarbomagnesiation of 1‑Halocyclopropenes · Figshare (2024) | TGRS Research Map | TGRS