Related Experiment Video
Updated: May 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Photochemical Switchable Access to Spiro-γ-lactams and Spiro-γ-lactones from Olefins via a N to O Atom Swap
Saradindu Debnath1, Mahadev Ray1, Soumitra Maity1
1Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Dhanbad, Jharkhand 826004, India.
Abstract:
A chemodivergent platform for the synthesis of spirolactams and spirolactones has not been devised to date due to the inherent difference in the heteroatom (N vs O). Major challenges include finding a suitable N to O atom swap strategy and tactical reagent design. Herein, we describe a visible-light-mediated strategy that can install both spiro-γ-lactams and lactones onto olefins from suitable oxime esters via a merger with a N to O atom swap. This exchange is achieved by the venerated diazotization reaction, providing a rare example of its application to nonaromatic amines.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Thermal Sigmatropic Reactions: Overview
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred to as...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Cycloaddition Reactions: MO Requirements for Photochemical Activation
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
![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)