"Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaterna" by Joshua A. Malone, Satish Chandra Philkhana et al.

Faculty Publications

Title

Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones

Authors

Joshua A. Malone, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Satish Chandra Philkhana, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Jacob R. Stepherson, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Fatimat O. Badmus, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Frank R. Fronczek, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Rendy Kartika, Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.

Document Type

Article

Publication Date

7-8-2022

Abstract

We describe a new synthetic reaction that generates all-carbon bis-quaternary centers at the opposing side of α-carbons in cyclohexanone with four different substituents in a controlled manner. Catalyzed by Cu(MeCN)BF salt, this chemistry is proposed to proceed via an intermediacy of unsymmetrical -allyl oxyallyl cations, which undergo a sequence of regioselective nucleophilic addition with substituted indoles and diastereoselective Claisen rearrangement in a single synthetic operation. The stereochemical outcome of the products features the diastereorelationship between the two aryl groups at the α,α'-positions.

Publication Source (Journal or Book title)

Organic letters

First Page

4810

Last Page

4815

Recommended Citation

Malone, J. A., Philkhana, S. C., Stepherson, J. R., Badmus, F. O., Fronczek, F. R., & Kartika, R. (2022). Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones. Organic letters, 24 (26), 4810-4815. https://doi.org/10.1021/acs.orglett.2c01890

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