Base-Mediated Substrate-Dependent [2 + 3] and [3 + 3] Annulation of Bisnucleophiles: Enabling the Modular Synthesis
Jiaxu Feng1,2, Yingying Wu1, Lulu Xu1
1Department of Chemistry, College of Sciences, Tianjin University of Science &Technology, Tianjin 300457, People's Republic of China.
Abstract:
Herein, we represented two facile and efficient approaches for the synthesis of functionalized spirocyclopentane oxindoles and tetrahydro-α-carbolines from different bisnucleophiles with 3-iodo-2-iodomethyl-1-propene via [2 + 3] and [3 + 3] annulation. These methods exhibit good functional group tolerances, simple conditions, easily available start materials, and moderate to good yields.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

![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)
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)