Related Experiment Video
Updated: Feb 6, 2026
06:44
Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
Published on: April 6, 2017
10.2K
An amine protecting group deprotectable under nearly neutral oxidative conditions
Shahien Shahsavari1, Chase McNamara1, Mark Sylvester1
1Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA.
Beilstein Journal of Organic Chemistry
|August 17, 2018
Summary
A novel 1,3-dithiane-based dM-Dmoc group effectively protects amino groups under various conditions. This new protecting group offers unique deprotection orthogonality for advanced synthetic chemistry applications.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Amino group protection is crucial in organic synthesis.
- Existing protecting groups have limitations in orthogonality and reaction conditions.
Purpose of the Study:
- To investigate the efficacy of the 1,3-dithiane-based dM-Dmoc group for amino protection.
- To evaluate its performance under different reaction conditions and assess deprotection strategies.
Main Methods:
- Protection of aliphatic and arylamines using the dM-Dmoc group.
- Optimization of reaction conditions for both amine types.
- Development of a deprotection protocol involving oxidation and base treatment.
Main Results:
- Successful protection of aliphatic amines under mild conditions.
- Effective protection of less reactive arylamines under more reactive conditions.
- Moderate to excellent yields achieved for both protection and deprotection steps.
Conclusions:
- The dM-Dmoc group provides a new orthogonal protecting strategy for amines.
- Its distinct deprotection conditions enable transformations not possible with current groups.
- This offers expanded possibilities in complex molecule synthesis.
Related Concept Videos
03:14Oxidation Numbers
42.9K
In redox reactions, the transfer of electrons occurs between reacting species. Electron transfer is described by a hypothetical number called the oxidation number (or oxidation state). It represents the effective charge of an atom or element, which is assigned using a set of rules.
42.9K
03:11Oxidation-Reduction Reactions
75.8K
Oxidation–Reduction Reactions
75.8K
01:19Amines to Amides: Acylation of Amines
3.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.5K
01:30Preparation of Amines: Alkylation of Ammonia and Amines
4.7K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
4.7K
03:26Acids, Bases and Neutralization Reactions
63.8K
An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
63.8K
01:15Pyruvate Oxidation
169.0K
After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
First, the enzyme pyruvate dehydrogenase removes the carboxyl group from pyruvate and releases it as carbon dioxide. The stripped molecule is then oxidized and releases electrons, which are then picked up by NAD+...
First, the enzyme pyruvate dehydrogenase removes the carboxyl group from pyruvate and releases it as carbon dioxide. The stripped molecule is then oxidized and releases electrons, which are then picked up by NAD+...
169.0K