Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines

Xavier Verdaguer1, Udo E W Lange1, Stephen L Buchwald1

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA), Fax: (+1) 617-253-3297.

Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.5K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
6.7K
The Scope of Physics01:17

The Scope of Physics

Physics is concerned with the interactions of energy, matter, space, and time, in order to discover the underlying mechanisms that underpin all phenomena. The word "physics" comes from the Greek word "phúsis", which means nature. Physics seeks to comprehend the natural world around us at its most fundamental level. It emphasizes the use of quantitative laws to do this, which could be valuable in other fields that want to push the performance boundaries of present...
53.5K
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...
4.4K
Rotation of Asymmetric Top01:11

Rotation of Asymmetric Top

By definition, a spherically symmetric body has the same moment of inertia about any axis passing through its center of mass. This situation changes if there is no spherical symmetry. Since most rigid bodies are not spherically symmetric, these require special treatment.
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
1.6K
Asymmetric Lipid Bilayer01:35

Asymmetric Lipid Bilayer

Biological membranes show uneven distribution of different types of lipids in the inner and outer layers, resulting in transverse asymmetric membranes. The treatment of the erythrocyte membrane with the enzyme phospholipase confirmed the asymmetric nature of the lipid bilayer. The enzyme hydrolyzes lipids into fatty acids and hydrophilic groups. The phospholipase acts only on the outer layer of the membrane, while the inner layer remains intact. The phospholipase treatment resulted in 80%...
9.9K