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

25 October 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review 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

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Supporting Information
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Experimental procedures Spectroscopic Data (1H HMR, 13C NMR , HRMS) and spectral reprints (1H NMR and 13C NMR)
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Grenning Research Lab
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Grenning Research Lab Website
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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

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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.

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