Related Experiment Video
Updated: Sep 19, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic Intramolecular Reductive Amination Using Secondary Amines: Expanding Access to Chiral Tertiary Amine
Longxue Xiang1, Cai You2, Xiuxiu Li1
1Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, People's Republic of China.
Abstract:
An unprecedented intramolecular asymmetric reductive amination that employs secondary amines as the nitrogen source, an important and persistent challenge in reductive amination, has been developed. This breakthrough broadens the synthetic scope, enabling the efficient construction of chiral tertiary amine-containing heterocycles, a crucial class of chiral amines. A tailored ZhaoPhos-based diphosphine ligand, distinct from commercial diphosphines, in combination with an iridium precursor delivers excellent catalytic activity and enantioselectivity. The synthetic utility of this approach is highlighted by the concise and scalable enantioselective synthesis of nicotinic alkaloids with significant medicinal value.
Related Concept Videos
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
![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)
