The control of stereochemistry by the pentafluorosulfanyl group

Paul R. Savoie; Cortney N. Von Hahmann; Alexander Penger; Zheng Wei; John T. Welch

doi:10.1039/c7ob03146g

The control of stereochemistry by the pentafluorosulfanyl group

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

Chemistry

University at Albany

SUNY Albany

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

10 Scopus citations

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.

Original language	English
Pages (from-to)	3151-3159
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	17
DOIs	https://doi.org/10.1039/c7ob03146g
State	Published - 2018

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title = "The control of stereochemistry by the pentafluorosulfanyl group",

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.",

author = "Savoie, \{Paul R.\} and \{Von Hahmann\}, \{Cortney N.\} and Alexander Penger and Zheng Wei and Welch, \{John T.\}",

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doi = "10.1039/c7ob03146g",

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pages = "3151--3159",

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T1 - The control of stereochemistry by the pentafluorosulfanyl group

AU - Savoie, Paul R.

AU - Von Hahmann, Cortney N.

AU - Penger, Alexander

AU - Wei, Zheng

AU - Welch, John T.

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85046647451

U2 - 10.1039/c7ob03146g

DO - 10.1039/c7ob03146g

M3 - Article

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SN - 1477-0520

VL - 16

SP - 3151

EP - 3159

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

The control of stereochemistry by the pentafluorosulfanyl group

Abstract

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