Related Experiment Video
Updated: May 20, 2025

Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
Published on: November 11, 2008
The Versatility of the Roskamp Homologation in Synthesis
Margherita Miele1, Aljoša Smajić2, Vittorio Pace1,2
1Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy.
Abstract:
Modern organic synthesis continues to benefit from the flexibility of α-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction-first introduced in 1989-has become a valuable tool due to its selectivity and mild condition reactions for accessing important synthons amenable to further functionalization as β-keto esters. The fine-tuning of reaction parameters-including the nature of Lewis acids, solvents, and temperature-has enabled the development of catalyzed continuous-flow methodologies, as well as a series of asymmetric variants characterized by high transformation rates, excellent stereocontrol, and formidable chemoselectivity. This review aims to emphasize the attractive features of the Roskamp reaction and its applicability for addressing challenging homologation processes.
Related Concept Videos
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
![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)
