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Huai-Ri Sun¹, Qingyang Zhao², Hui Yang¹

¹Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China.

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|August 16, 2019

Summary

This summary is machine-generated.

A new asymmetric Prins cyclization reaction efficiently synthesizes functionalized tetrahydroquinoline derivatives. This method uses chiral phosphoric acid, achieving high yields and stereoselectivities for complex molecules.

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Area of Science:

Organic Chemistry
Catalysis
Medicinal Chemistry

Background:

Quinone methides and o-aminobenzaldehyde are key precursors in organic synthesis.
Asymmetric catalysis is crucial for developing enantiomerically pure compounds.
Tetrahydroquinoline derivatives possess significant biological and pharmaceutical relevance.

Purpose of the Study:

To develop an efficient asymmetric Prins cyclization for synthesizing trans-fused pyrano-/furo-tetrahydroquinoline derivatives.
To utilize chiral phosphoric acid as a catalyst for high stereoselectivity.
To explore an unconventional synthetic route for complex heterocyclic compounds.

Main Methods:

In situ generation of quinone methides.
Asymmetric Prins cyclization reaction catalyzed by chiral phosphoric acid.
Purification and characterization of the synthesized tetrahydroquinoline derivatives.

Main Results:

The developed method provides facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives.
Excellent yields (up to 99%) and high diastereoselectivity and enantioselectivity (up to 99% ee) were achieved.
Mechanistic studies elucidated the sequential formation of C-O, C-C, and C-N bonds for constructing three adjacent tertiary stereocenters.

Conclusions:

The asymmetric Prins cyclization offers a powerful and efficient strategy for synthesizing complex tetrahydroquinoline scaffolds.
Chiral phosphoric acid serves as a highly effective catalyst for achieving exceptional stereocontrol.
This methodology opens new avenues for the discovery of novel bioactive compounds containing the tetrahydroquinoline core.