Synthesis of two reagents for an efficient separation of chemical intermediates

Challenges

The challenges for this kind of synthesis are:

• The difficulty in effectively separating racemic enantiomers under mild conditions
• The limited availability of chiral reagents
• The need to optimize yields without compromising enantiomeric purity
• The complexity in managing multi-step processes with broad substrate compatibility

Innovative solution

Unique chiral reagent enabling both separation and deoxygenation of racemic alcohols in two steps.

Applications

• Synthesis of complex bioactive molecules,

• pharmaceuticals,

• fine chemistry,

• multi-step synthesis,

• agrochemicals

COMPETITIVE ADVANTAGES

• Easy enantiomer separation via silica gel purification
• Dual functionality: separation and deoxygenation
• Radical reaction tolerant to a wide range of substrates
• Time and step reduction in asymmetric synthesis
• Direct impact on the production of essential enantiopure molecules

How it works

The synthesis process of the separation agent, subject of the invention, allows for the production of two different reagents (3 and 9), which can be used depending on the alcohols to be separated.

In the example illustrated below, the synthesized reagent 9 is used on the alcohol 13: (+)-myrioneurinol. The two resulting diastereomers can then be separated. Finally, the Barton-McCombie reaction of each compound can be performed, with an excellent yield exceeding 90%.

DEVELOPMENT STATUS - TRL 3