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. 2024 May 22;146(20):13748-13753.
doi: 10.1021/jacs.4c04438. Epub 2024 May 9.

Synthesis of Stereodefined Polysubstituted Bicyclo[1.1.0]butanes

Rahul Suresh  1 , Noam Orbach  1 , Ilan Marek  1
Affiliations

Synthesis of Stereodefined Polysubstituted Bicyclo[1.1.0]butanes

Rahul Suresh et al. J Am Chem Soc. .

Erratum in

Abstract

We report a highly diastereoselective synthesis of polysubstituted bicyclobutanes possessing up to three stereodefined quaternary centers and five substituents. Our strategy involves a diastereoselective carbometalation of cyclopropenes followed by a cyclization to furnish the bicyclobutane ring system. This straightforward approach allows for the incorporation of a diverse range of substituents and functional groups, notably without the need for electron-withdrawing functionalities.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Synthetic Routes to Substituted BCBs
Scheme 2
Scheme 2. Proposed Strategy
Scheme 3
Scheme 3. Diastereoselective Preparation of Polysubstituted Bromomethyl–iodocyclopropanes
Scheme 4
Scheme 4. Synthesis of Polysubstituted BCBs
Yields were measured using 1H NMR with tert-butyl methyl ether as the internal standard.
Scheme 5
Scheme 5. Synthesis of Enantioenriched BCB
Yields were measured using 1H NMR with tert-butyl methyl ether as the internal standard.
Scheme 6
Scheme 6. Synthesis of Pentasubstituted BCB
Yields were measured using 1H NMR with tert-butyl methyl ether as the internal standard.
See this image and copyright information in PMC

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