The control of stereochemistry by the pentafluorosulfanyl group

Literature Information

Publication Date 2018-04-07
DOI 10.1039/C7OB03146G
Impact Factor 3.876
Authors

Paul R. Savoie, Cortney N. von Hahmann, Alexander Penger, Zheng Wei, John T. Welch


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Abstract

The influence of pentafluorosulfanylation on biological activity has been revealed in numerous comparative studies of biologically active compounds, but considerably less is known about the influence of pentafluorosulfanylation on reactivity. Among the distinctive properties of the pentafluorosulfanyl group is the profound dipole moment that results from introduction of this substituent. It has been shown that dipolar effects coupled with the steric demand of the SF5 group may be employed to influence the stereochemistry of reactions, especially those processes with significant charge separation in the transition state. The Staudinger ketene-imine cycloaddition reaction is an ideal platform for investigation of dipolar control of diastereoselectivity by the pentafluorosulfanyl group.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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