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Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Synthesis of β-Lactams

preprint
submitted on 26.12.2019 and posted on 27.12.2019 by Christopher M. Poteat, Yujin Jang, Myunggi Jung, John D. Johnson, Rachel G. Williams, Vincent Lindsay
Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates due to their extreme strain and kinetic instability. Herein, we report the enantioselective synthesis of 1-sulfonylcyclopropanols as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, via α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as electrophilic oxygen source. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone, highlighting the modular nature of these precursors and the potential for their widespread adoption as synthetic intermediates. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines acting here as nitrene equivalents, leading to the efficient formation of chiral β-lactam derivatives.

History

Email Address of Submitting Author

vlindsa@ncsu.edu

Institution

North Carolina State University

Country

United States

ORCID For Submitting Author

0000-0002-7126-325X

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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