Diastereoselective (3 + 3)-Annulations of Trisubstituted Michael Acceptors for Access to Polyfunctional Cyclohexanones

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Mar 19

PMID 38501591

Authors

Katelyn M Kitzinger

Mitchell T Giordano

Pedro de Jesus Cruz

Jeffrey S Johnson

Affiliations

Soon will be listed here.

Abstract

Michael-aldol domino reactions are powerful tools for rapidly assembling carbocyclic scaffolds. We herein disclose a base-catalyzed Michael-aldol domino reaction of trisubstituted Michael acceptors with β-keto ester nucleophiles. The cyclohexanone products are obtained in excellent diastereoselectivity (up to >20:1 dr) and good yields (up to 84%). An attractive practical consideration is that pure products are isolated directly via filtration of the unpurified reaction mixtures. Further functionalization of the cyclohexanones is achieved without perturbation of stereocenters installed through the preceding annulation.

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