Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes

Yair Cohen; Ilan Marek

doi:10.1002/anie.202111382

Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes

Yair Cohen
, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

A regio- and diastereoselective copper-catalyzed carbomagnesiation of 1,2-dialkylated cyclopropenes is reported. The regioselectivity is controlled by a subtle tethered Lewis basic moiety. The chelating moieties allow the differentiation between two electronically tantamount organometallic intermediates. Further functionalization grants access to polysubstituted stereodefined cyclopropanes bearing up to five alkyl groups.

Original language	English
Pages (from-to)	26368-26372
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	50
DOIs	https://doi.org/10.1002/anie.202111382
State	Published - 7 Oct 2021

Keywords

carbon quaternary stereocenters
copper-catalyzed carbomagnesiation
directing group
regioselectivity

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.202111382

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title = "Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes",

abstract = "A regio- and diastereoselective copper-catalyzed carbomagnesiation of 1,2-dialkylated cyclopropenes is reported. The regioselectivity is controlled by a subtle tethered Lewis basic moiety. The chelating moieties allow the differentiation between two electronically tantamount organometallic intermediates. Further functionalization grants access to polysubstituted stereodefined cyclopropanes bearing up to five alkyl groups.",

keywords = "carbon quaternary stereocenters, copper-catalyzed carbomagnesiation, directing group, regioselectivity",

author = "Yair Cohen and Ilan Marek",

note = "Funding Information: This project has received funding from the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (Grant No. 330/17). Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

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T1 - Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes

AU - Cohen, Yair

AU - Marek, Ilan

N1 - Funding Information: This project has received funding from the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (Grant No. 330/17). Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/10/7

Y1 - 2021/10/7

N2 - A regio- and diastereoselective copper-catalyzed carbomagnesiation of 1,2-dialkylated cyclopropenes is reported. The regioselectivity is controlled by a subtle tethered Lewis basic moiety. The chelating moieties allow the differentiation between two electronically tantamount organometallic intermediates. Further functionalization grants access to polysubstituted stereodefined cyclopropanes bearing up to five alkyl groups.

AB - A regio- and diastereoselective copper-catalyzed carbomagnesiation of 1,2-dialkylated cyclopropenes is reported. The regioselectivity is controlled by a subtle tethered Lewis basic moiety. The chelating moieties allow the differentiation between two electronically tantamount organometallic intermediates. Further functionalization grants access to polysubstituted stereodefined cyclopropanes bearing up to five alkyl groups.

KW - carbon quaternary stereocenters

KW - copper-catalyzed carbomagnesiation

KW - directing group

KW - regioselectivity

UR - https://www.scopus.com/pages/publications/85118526482

U2 - 10.1002/anie.202111382

DO - 10.1002/anie.202111382

M3 - Article

SN - 1433-7851

VL - 60

SP - 26368

EP - 26372

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 50

ER -

Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes

Abstract

Keywords

ASJC Scopus subject areas

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