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

Hebrew University of Jerusalem

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

8 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
Externally published	Yes

Bibliographical note

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

Funding

This research was supported by a grant from the Israel Science Foundation (Grant No. 287/21). We thank Dr. Benny Bogoslavsky (The Hebrew University of Jerusalem, Israel) for the X‐ray structure determination. N. H. and M. N. are grateful for a fellowship from The Hebrew University of Jerusalem. N. E. is thankful for a Ph.D. fellowship from the Neubauer Foundation.

Funders	Funder number
Neubauer Foundation
Hebrew University of Jerusalem
Israel Science Foundation	287/21

Keywords

cyclopropanation
diazoacetates
gem-dibroylalkanes
organoborones
stereodivergent-strategy.

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10.1002/chem.202202748

Cite this

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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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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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A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes

Abstract

Bibliographical note

Funding

Keywords

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