Design and Synthesis of a Ferrocene-Based Diol Library and Application in the Hetero-Diels-Alder Reaction

Diol scaffolds have been utilized as highly effective catalysts and ligands in a wide range of catalytic asymmetric transformations. For scaffolds to be successful as broadly used motifs, they should be prepared cheaply through facile routes and be easily handled. Herein, the synthesis of a family of planar chiral diols based on a modular and robust threestep route is described, which yields catalytically active diols in >99% de and >99% ee, with up to seven different chiral elements. These diols have been characterized by X-ray crystallographic analysis, which provides clear evidence for the likely transition state when applied in the asymmetric hetero-Diels-Alder reaction. Without altering the stereochemistry of the catalyst backbone, it is possible to access both enantiomers of the product by varying the substitution of the catalyst at the alpha-position.

Automated summary

This article describes the synthesis of planar chiral diols through a simple route, which are catalytically active and produce highly selective products in asymmetric reactions. The likely transition state is confirmed by X-ray crystallographic analysis, and both enantiomers of the product can be obtained by varying the substitution of the catalyst.