Publication

Site selective substitution of carbamate and carbamoyl protected benzylamines

Manfred Schlosser
1993
Journal Articles

Abstract

Methoxy- and fluoro-substituted benzylamines can be metalated optionally at the position adjacent to the nitrogen bearing side chain or adjacent to the hetero substituent as a function of the acyl-type protective group. Thus, lithiation of 2-FC6H4CH2NHBOC with BuLi/KOCMe3 in THF followed by carboxylation with CO2 and acid workup afforded 50% 2,3-F(HO2C)C6H3CH2NHBOC, whereas lithiation of 2-FC6H4CH2NHCONMe2 with LiCMe3 in THF followed by carboxylation afforded 81% 2,6-F(HO2C)C6H3CH2NHCONMe2 regioselectively. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/fb0f995f-67a3-466a-bfa3-7a67cd726551

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Manfred Schlosser
1993
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fb0f995f-67a3-466a-bfa3-7a67cd726551

About this result

Related concepts (9)

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.

Skeletal formula

The skeletal formula, or line-angle formula or shorthand formula, of an organic compound is a type of molecular structural formula that serves as a shorthand representation of a molecule's bonding and some details of its molecular geometry. A skeletal formula shows the skeletal structure or skeleton of a molecule, which is composed of the skeletal atoms that make up the molecule. It is represented in two dimensions, as on a piece of paper. It employs certain conventions to represent carbon and hydrogen atoms, which are the most common in organic chemistry.

Ketone

In organic chemistry, a ketone ˈkiːtoʊn is a functional group with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.