How to Submit
Browse
Events
Communities
About

Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement

25 October 2021, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers in the range of ~23 kcal/mol with isothermic favorability (G ~0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

Keywords

Cope Rearrangement
drug-like molecules
malononitrile
Reductive Cope Rearrangement

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental procedures Spectroscopic Data (1H HMR, 13C NMR , HRMS) and spectral reprints (1H NMR and 13C NMR)
Actions

Supplementary weblinks

Title
Description
Actions
Title
Grenning Research Lab
Description
Grenning Research Lab Website
Actions
View

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting and Discussion Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Now Published

Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement [opens in a new tab]
Kristin M. Sobie, Matthew Albritton, Yinuo Yang, Mariana M. Alves, Adrian Roitberg, Alexander J. Grenning journal article
Chemical Science , Volume 13, Issue 7
Online publication date: 2022

Version History

Oct 25, 2021 Version 1

Metrics

1,666
589
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-rff1d
D O I: 10.26434/chemrxiv-2021-rff1d [opens in a new tab]

Funding

National Institute of General Medical Sciences
R35 GM137893-01

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

Share