Related Experiment Video
Updated: Aug 26, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
A Missing Link in Multisubstituted Pyrrolidines: Remote Stereocontrol Forged by Rhodium-Alkyl Nitrene
Xinxin Tang1, Raj K Tak1, Hidetoshi Noda1
1Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan.
Abstract:
Pyrrolidines are significant N-heterocycles in medicinal chemistry and are among the top ten ring systems found in drug molecules. While simple derivatives are commercially available, densely decorated derivatives with precise stereochemical arrangements remain difficult to obtain. Methods for synthesizing multisubstituted pyrrolidines with nonadjacent stereocenters are particularly scarce. To bridge this gap, we report the stereoselective synthesis of remotely decorated, trisubstituted β-prolines via Rh-catalyzed C-H amination. The transformation proceeds well in the presence of various functionalities with exclusive anti-selectivity. Carboxylic acids in the products serve as gateways for diverse downstream transformations. Furthermore, the combined experimental and computational study sheds lights on the origin of high diastereoselectivity.
Related Concept Videos
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Nucleophilic Aromatic Substitution: Elimination–Addition
Radical Substitution: Allylic Bromination
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
