Chiral spirodihydroindene skeleton compound and preparation method thereof

Chiral fused-ring spirodihydroindene framework compounds were prepared by intramolecular Fourier-Kroughs reaction and asymmetric hydrogenation reaction using Brønsted acid or Lewis acid catalysts. This solved the problems of high cost and low efficiency in existing technologies and achieved a highly efficient and environmentally friendly asymmetric catalytic effect.

CN106365949AActive Publication Date: 2017-02-01SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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Patent Information

Application Number
CN201510974151.1
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2015-07-23
Filing Date
2015-12-22
Publication Date
2017-02-01
Estimated Expiration
2035-12-22

AI Technical Summary

Technical Problem

Existing methods for preparing chiral spirodihydroindene framework compounds require expensive chiral starting materials or chiral resolving reagents, involve cumbersome steps, are costly, and have low catalytic efficiency, making it difficult to achieve efficient and environmentally friendly asymmetric catalysis.

Method used

Chiral fused-ring spirodihydroindene framework compounds were prepared by employing intramolecular Fourier-Kroughs reactions and asymmetric hydrogenation reactions, using Brønsted or Lewis acids as catalysts, without the need for chiral starting materials or resolving reagents, and achieved efficient catalysis through transition metal catalysts.

Benefits of technology

We have achieved the preparation of chiral fused-ring spirodihydroindene framework compounds with high yield (>99%) and high optical purity (>99% ee value), which simplifies the process, reduces costs, and improves catalytic efficiency.

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Abstract

The invention discloses a chiral spirodihydroindene skeleton compound and a preparation method thereof. The chiral spirodihydroindene skeleton compound is represented by formula I or I'. The preparation method of the chiral spirodihydroindene skeleton compound is characterized in that an intramolecular Friedel-Crafts reaction of a compound represented by formula III is carried out in a solvent under the action of a catalyst to prepare the compound represented by formula I, and the catalyst is a Bronsted acid or a Lewis acid. The preparation method has the advantages of no chiral initial raw material or chiral resolution reagent, no chiral resolution steps, simplicity, simplicity in post-treatment, good economic property, environmental protection, high product yield, and realization of high optical purity and high chemical purity of the product. Transition metal catalyzed asymmetric reaction catalysts prepared by adopting the chiral spirodihydroindene skeleton compound have a substantial catalysis effect, the product yield is greater than 99%, and the ee value of the product higher than 99%.
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