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Emergence of single-molecular chirality from achiral reactants.

Steendam RR, Verkade JM, van Benthem TJ, Meekes H, van Enckevort WJ, Raap J, Rutjes FP, Vlieg E - Nat Commun (2014)

Bottom Line: The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life.We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction.An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal-solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state.

View Article: PubMed Central - PubMed

Affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

ABSTRACT
The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal-solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.

Show MeSH
Reaction of achiral reactants 2 and 3 under achiral conditions to furnish product 1.In solution, both product enantiomers (R-1 and S-1) are obtained in equal amounts. With the combination of crystals and solution, an enantiopure solid product can be obtained.
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f1: Reaction of achiral reactants 2 and 3 under achiral conditions to furnish product 1.In solution, both product enantiomers (R-1 and S-1) are obtained in equal amounts. With the combination of crystals and solution, an enantiopure solid product can be obtained.

Mentions: We demonstrate this novel route to single chirality through the synthesis of the chiral amine 1 (Fig. 1). This product is formed directly in an aza-Michael reaction from the achiral reactants p-anisidine (2) and α,β-unsaturated ketone (3) using an achiral catalyst.


Emergence of single-molecular chirality from achiral reactants.

Steendam RR, Verkade JM, van Benthem TJ, Meekes H, van Enckevort WJ, Raap J, Rutjes FP, Vlieg E - Nat Commun (2014)

Reaction of achiral reactants 2 and 3 under achiral conditions to furnish product 1.In solution, both product enantiomers (R-1 and S-1) are obtained in equal amounts. With the combination of crystals and solution, an enantiopure solid product can be obtained.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4263183&req=5

f1: Reaction of achiral reactants 2 and 3 under achiral conditions to furnish product 1.In solution, both product enantiomers (R-1 and S-1) are obtained in equal amounts. With the combination of crystals and solution, an enantiopure solid product can be obtained.
Mentions: We demonstrate this novel route to single chirality through the synthesis of the chiral amine 1 (Fig. 1). This product is formed directly in an aza-Michael reaction from the achiral reactants p-anisidine (2) and α,β-unsaturated ketone (3) using an achiral catalyst.

Bottom Line: The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life.We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction.An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal-solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state.

View Article: PubMed Central - PubMed

Affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

ABSTRACT
The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal-solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.

Show MeSH