Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Jan 4;60(1):212-216.
doi: 10.1002/anie.202011739. Epub 2020 Oct 28.

α-Selective Ring-Opening Reactions of Bicyclo[1.1.0]butyl Boronic Ester with Nucleophiles

Lin Guo  1 , Adam Noble  1 , Varinder K Aggarwal  1
Affiliations

α-Selective Ring-Opening Reactions of Bicyclo[1.1.0]butyl Boronic Ester with Nucleophiles

Lin Guo et al. Angew Chem Int Ed Engl. .

Abstract

The reaction of bicyclo[1.1.0]butyl pinacol boronic ester (BCB-Bpin) with nucleophiles has been studied. Unlike BCBs bearing electron-withdrawing groups, which react with nucleophiles at the β-position, BCB-Bpin reacts with a diverse set of heteroatom (O, S, N)-centred nucleophiles exclusively at the α-position. Aliphatic alcohols, phenols, carboxylic acids, thiols and sulfonamides were found to be competent nucleophiles, providing ready access to α-heteroatom-substituted cyclobutyl boronic esters. In contrast, sterically hindered bis-sulfonamides and related nucleophiles reacted with BCB-Bpin at the β'-position leading to cyclopropanes with high trans-selectivity. The origin of selectivity is discussed.

Keywords: 1,2-migration; boronic esters; cyclobutane; cyclopropane; strain release.

PubMed Disclaimer

References

    1. None
    1. K. B. Wiberg, G. M. Lampman, R. P. Ciula, D. S. Connor, P. Schertler, J. Lavanish, Tetrahedron 1965, 21, 2749-2769;
    1. J. Turkowska, J. Durka, D. Gryko, Chem. Commun. 2020, 56, 5718-5734.
    1. None
    1. S. Hoz, D. Aurbach, Tetrahedron 1979, 35, 881-883;

Publication types

LinkOut - more resources