A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes

Nicole Hanania; Molhm Nassir; Nadim Eghbarieh; Ahmad Masarwa

doi:10.1002/chem.202202748

A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes

Nicole Hanania, Molhm Nassir, Nadim Eghbarieh, Ahmad Masarwa^*

^*Corresponding author for this work

Institute of Chemistry

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

6 Scopus citations

Abstract

We report a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes. The reaction provides a highly modular approach to prepare cyclopropane ring variants bearing gem-(Bpin,Bpin), gem-(Bpin,Bdan), and gem-(Bpin,BF₃K), with outstanding levels of stereocontrol. This was achieved by diastereoselective Pd-catalyzed cyclopropanation reactions of gem-diborylalkenes with α-diazoarylacetates and α-diazoaryl-trifluoromethyl. The key to the success of this general protocol was the diastereoselective trifluorination reaction of gem-diborylcyclopropanes, followed by the stereospecific interconversion of the trifluoroborate salts into the Bdan group.

Original language	English
Article number	e202202748
Journal	Chemistry - A European Journal
Volume	28
Issue number	72
DOIs	https://doi.org/10.1002/chem.202202748
State	Published - 27 Dec 2022

Bibliographical note

Publisher Copyright:
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

cyclopropanation
diazoacetates
gem-dibroylalkanes
organoborones
stereodivergent-strategy.

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10.1002/chem.202202748

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title = "A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes",

abstract = "We report a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes. The reaction provides a highly modular approach to prepare cyclopropane ring variants bearing gem-(Bpin,Bpin), gem-(Bpin,Bdan), and gem-(Bpin,BF3K), with outstanding levels of stereocontrol. This was achieved by diastereoselective Pd-catalyzed cyclopropanation reactions of gem-diborylalkenes with α-diazoarylacetates and α-diazoaryl-trifluoromethyl. The key to the success of this general protocol was the diastereoselective trifluorination reaction of gem-diborylcyclopropanes, followed by the stereospecific interconversion of the trifluoroborate salts into the Bdan group.",

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author = "Nicole Hanania and Molhm Nassir and Nadim Eghbarieh and Ahmad Masarwa",

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AU - Hanania, Nicole

AU - Nassir, Molhm

AU - Eghbarieh, Nadim

AU - Masarwa, Ahmad

PY - 2022/12/27

Y1 - 2022/12/27

N2 - We report a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes. The reaction provides a highly modular approach to prepare cyclopropane ring variants bearing gem-(Bpin,Bpin), gem-(Bpin,Bdan), and gem-(Bpin,BF3K), with outstanding levels of stereocontrol. This was achieved by diastereoselective Pd-catalyzed cyclopropanation reactions of gem-diborylalkenes with α-diazoarylacetates and α-diazoaryl-trifluoromethyl. The key to the success of this general protocol was the diastereoselective trifluorination reaction of gem-diborylcyclopropanes, followed by the stereospecific interconversion of the trifluoroborate salts into the Bdan group.

AB - We report a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes. The reaction provides a highly modular approach to prepare cyclopropane ring variants bearing gem-(Bpin,Bpin), gem-(Bpin,Bdan), and gem-(Bpin,BF3K), with outstanding levels of stereocontrol. This was achieved by diastereoselective Pd-catalyzed cyclopropanation reactions of gem-diborylalkenes with α-diazoarylacetates and α-diazoaryl-trifluoromethyl. The key to the success of this general protocol was the diastereoselective trifluorination reaction of gem-diborylcyclopropanes, followed by the stereospecific interconversion of the trifluoroborate salts into the Bdan group.

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KW - diazoacetates

KW - gem-dibroylalkanes

KW - organoborones

KW - stereodivergent-strategy.

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A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes

Abstract

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Keywords

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