Diastereoselective (3 + 3)-Annulations of Trisubstituted Michael Acceptors for Access to Polyfunctional
Katelyn M Kitzinger1, Mitchell T Giordano1, Pedro de Jesús Cruz1
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
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.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: MO Requirements for Thermal Activation

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
