The control of stereochemistry by the pentafluorosulfanyl group

文献信息

发布日期 2018-04-07

DOI 10.1039/C7OB03146G

影响因子 3.876

作者

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

查看原文

摘要

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.

期刊推荐

Dental Materials

Applied Clay Science

Studies in Conservation

Drug and Chemical Toxicology

Synthetic Communications

Journal of Natural Products

European Journal of Medicinal Chemistry

Dyes and Pigments

Tetrahedron Letters

Organic Geochemistry

相关文献

Targeting the RNA demethylase FTO for cancer therapy

2021-07-26 Review Article

DOI: 10.1039/D1CB00075F

A COVID-19 vaccine candidate composed of the SARS-CoV-2 RBD dimer and Neisseria meningitidis outer membrane vesicles‡

Darielys Santana-Mederos, Rocmira Perez-Nicado, Yanet Climent, Laura Rodriguez, Belinda Sanchez Ramirez, Sonia Perez-Rodriguez, Meybi Rodriguez, Claudia Labrada, Tays Hernandez, Marianniz Diaz, Ivette Orosa, Ubel Ramirez, Reynaldo Oliva, Raine Garrido, Felix Cardoso, Mario Landys, Roselyn Martinez, Humberto Gonzalez, Tamara Hernandez, Rolando Ochoa-Azze, Jose L. Perez, Juliet Enriquez, Nibaldo Gonzalez, Yenicet Infante, Luis A. Espinosa, Yassel Ramos, Luis Javier González, Carmen Valenzuela, Ana Victoria Casadesus, Briandy Fernandez, Gertrudis Rojas, Beatriz Pérez-Massón, Yaima Tundidor, Ernesto Bermudez, Claudia A. Plasencia, Tammy Boggiano, Eduardo Ojito, Sonsire Fernandez, Françoise Paquet, Cheng Fang, Guang-Wu Chen, Daniel G. Rivera, Yury Valdes-Balbin, Dagmar Garcia-Rivera, Vicente Verez Bencomo

2021-12-08 Paper

DOI: 10.1039/D1CB00200G

Inside front cover

Cover

DOI: 10.1039/D0CB90013C

Medicinal chemistry of the myeloid C-type lectin receptors Mincle, Langerin, and DC-SIGN

Jonathan Cramer

2021-09-16 Review Article

DOI: 10.1039/D1MD00238D

Modified nucleoside triphosphates in bacterial research for in vitro and live-cell applications

Adeline Espinasse, Hannah K. Lembke, Angela A. Cao

2020-09-14 Review Article

DOI: 10.1039/D0CB00078G

The chemical biology of coronavirus host–cell interactions

Suprama Datta, Erik C. Hett, Kalpit A. Vora, Rob C. Oslund, Olugbeminiyi O. Fadeyi, Andrew Emili

2020-12-23 Review Article

DOI: 10.1039/D0CB00197J

Epoxidation of 1-octene under harsh tail-end conditions in a flow reactor I: a comparative study of crystalline vs. amorphous catalysts

Martina Aigner, Nicolás Andrés Grosso-Giordano, Alexander Okrut, Stacey Zones, Alexander Katz

2017-07-26 Paper

DOI: 10.1039/C7RE00076F

Biosynthesis of alkyne-containing natural products

Xinyang Li, Jian-Ming Lv, Dan Hu

2020-12-21 Review Article

DOI: 10.1039/D0CB00190B

Metathramycin, a new bioactive aureolic acid discovered by heterologous expression of a metagenome derived biosynthetic pathway

Liwei Liu

2021-02-02 Paper

DOI: 10.1039/D0CB00228C

Measuring ROS and redox markers in plant cells

Edward N. Smith, Emily Flashman

2021-06-29 Review Article

DOI: 10.1039/D1CB00071C

来源期刊

Organic & Biomolecular Chemistry

CiteScore: 3.4

自引率: 10.3%

年发文量: 1041

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.