Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Tal Weissbrod; Alin Asraf; Ilan Marek

doi:https://doi.org/10.1021/acs.orglett.4c03507

Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Tal Weissbrod, Alin Asraf, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.4c03507
State	Accepted/In press - 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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https://doi.org/10.1021/acs.orglett.4c03507

Cite this

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title = "Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes",

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.",

author = "Tal Weissbrod and Alin Asraf and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

doi = "https://doi.org/10.1021/acs.orglett.4c03507",

language = "الإنجليزيّة",

journal = "Organic Letters",

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T1 - Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

AU - Weissbrod, Tal

AU - Asraf, Alin

AU - Marek, Ilan

PY - 2024

Y1 - 2024

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.

UR - http://www.scopus.com/inward/record.url?scp=85207143235&partnerID=8YFLogxK

U2 - https://doi.org/10.1021/acs.orglett.4c03507

DO - https://doi.org/10.1021/acs.orglett.4c03507

M3 - مقالة

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Copper-Catalyzed Carbomagnesiation of 1-Halocyclopropenes

Abstract

All Science Journal Classification (ASJC) codes

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