Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds

Kyla J. Woelk; Kushal Dhake; Nathan D. Schley; David C. Leitch

doi:10.1039/D3CC04234K

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds†

Kyla J. Woelk,^a Kushal Dhake,^a Nathan D. Schley

^b and David C. Leitch

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Victoria, 3800 Finnerty Rd., Victoria, BC, Canada
E-mail: dcleitch@uvic.ca

^b Department of Chemistry, Vanderbilt University, 2301 Vanderbilt Place, Nashville, TN, USA

Abstract

We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. Glycine-derived enolates directly give protected 2-oxo-3-amino-BCH derivatives that can be further functionalized. Arylacetate derivatives are also suitable enolate precursors, giving 2-oxo-3-aryl-BCH scaffolds from readily available starting materials.

This article is part of the themed collection: 2023 Emerging Investigators

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/D3CC04234K
Article type: Communication
Submitted: 29 8 2023
Accepted: 10 10 2023
First published: 10 10 2023

Download Citation

Chem. Commun., 2023,59, 13847-13850

Permissions

Request permissions

Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds

K. J. Woelk, K. Dhake, N. D. Schley and D. C. Leitch, Chem. Commun., 2023, 59, 13847 DOI: 10.1039/D3CC04234K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications

Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds

Social activity

Search articles by author

Spotlight

Advertisements