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

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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

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

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

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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

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Chemical Communications

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

Abstract

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

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