Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Tal Weissbrod; Alin Asraf; Ilan Marek

doi:10.1021/acs.orglett.4c03507

Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Tal Weissbrod
, Alin Asraf
, Ilan Marek

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

We report a versatile copper-catalyzed carbomagnesiation reaction of poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning the regioselectivity of the addition, we were able to access configurationally stable fully substituted cyclopropyl carbenoid intermediates. These intermediates were subsequently trapped with electrophiles to furnish stereodefined poly- and fully substituted halocyclopropyl esters. The regioselectivity of the addition was found to be dependent on the nature of the sp² substituents.

Original language	English
Pages (from-to)	9138-9141
Number of pages	4
Journal	Organic Letters
Volume	26
Issue number	42
DOIs	https://doi.org/10.1021/acs.orglett.4c03507
State	Published - 25 Oct 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c03507

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abstract = "We report a versatile copper-catalyzed carbomagnesiation reaction of poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning the regioselectivity of the addition, we were able to access configurationally stable fully substituted cyclopropyl carbenoid intermediates. These intermediates were subsequently trapped with electrophiles to furnish stereodefined poly- and fully substituted halocyclopropyl esters. The regioselectivity of the addition was found to be dependent on the nature of the sp2 substituents.",

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N2 - We report a versatile copper-catalyzed carbomagnesiation reaction of poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning the regioselectivity of the addition, we were able to access configurationally stable fully substituted cyclopropyl carbenoid intermediates. These intermediates were subsequently trapped with electrophiles to furnish stereodefined poly- and fully substituted halocyclopropyl esters. The regioselectivity of the addition was found to be dependent on the nature of the sp2 substituents.

AB - We report a versatile copper-catalyzed carbomagnesiation reaction of poly- and fully substituted 1-halocyclopropenyl esters. By fine-tuning the regioselectivity of the addition, we were able to access configurationally stable fully substituted cyclopropyl carbenoid intermediates. These intermediates were subsequently trapped with electrophiles to furnish stereodefined poly- and fully substituted halocyclopropyl esters. The regioselectivity of the addition was found to be dependent on the nature of the sp2 substituents.

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JO - Organic Letters

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Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Abstract

ASJC Scopus subject areas

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