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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Catalytic Enantioselective Biltz Synthesis.

Di Tian¹, Zhuo-Chen Li¹, Ze-Hua Sun²

¹Shanghai Frontiers Science Center for Drug Target Identification and Delivery, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, 800 Dongchuan Road, Minhang District, Shanghai, 200240, China.

Angewandte Chemie (International Ed. in English)

|October 10, 2023

Summary

This study presents the first enantioselective catalytic Biltz synthesis, enabling efficient production of diverse thiohydantoins with excellent stereochemical control. The method also allows for a one-pot synthesis of hydantoins.

Keywords:

(Thio)Hydantoins Asymmetric 1,2-Rearrangement Aza-Quaternary Stereocenter Biltz Synthesis Cascade Reaction

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Published on: November 27, 2015

Area of Science:

Organic Chemistry
Asymmetric Catalysis
Synthetic Methodology

Background:

The Biltz synthesis provides access to 5,5-disubstituted (thio)hydantoins from 1,2-diketones and (thio)ureas.
This reaction is known for atom and step economy, but lacks stereochemical control.

Purpose of the Study:

To develop the first enantioselective catalytic Biltz synthesis.
To achieve high stereo- and regio-control in the synthesis of thiohydantoins.
To enable a one-pot synthesis of corresponding hydantoins.

Main Methods:

Enantioselective catalysis
Biltz synthesis using 1,2-diketones and thioureas
Density Functional Theory (DFT) calculations
Experimental studies

Main Results:

Developed the first enantioselective catalytic Biltz synthesis.
Synthesized over 40 thiohydantoins with high stereo- and regio-control.
Achieved high stereoselectivity regardless of thiourea symmetry.
Demonstrated a one-pot synthesis for hydantoins.
Elucidated the reaction pathway and origin of stereoselectivity via experimental and computational studies.

Conclusions:

The developed method offers a significant advancement in asymmetric synthesis.
Provides a versatile route to enantiomerically enriched (thio)hydantoins.
The mechanistic insights deepen the understanding of asymmetric Biltz reactions.