Enantioselective formal [3+2]-cycloadditions to access spirooxindoles bearing four contiguous stereocenters through
Jun-An Xiao1, Jin-Lian Li1, Xiu-Liang Cheng1
1Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. China. jaxiao@nnnu.edu.cn huangyanmin828@163.com.
Abstract:
An enantioselective ring-opening formal [3+2]-cycloaddition of spirovinylcyclopropyl oxindoles with enals via synergistic catalysis of palladium(0) and a chiral organocatalyst has been developed, affording spirooxindoles bearing four contiguous stereocenters in good yields with excellent enantioselectivities. The generality and utility of the protocol were also demonstrated through scale-up experiments and synthetic transformation of the resulting cycloadduct.
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
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)
