Proline sulfinamide double-chirality organic molecular catalyst and preparation method thereof

A technology of proline sulfenamide and proline formamide trifluoroacetate, which is applied in the field of bichiral organic small molecule catalysts and its preparation, and achieves the effects of easy-to-obtain raw materials, simple operation and wide application

Inactive Publication Date: 2014-02-19
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, chiral tert-butylsulfinamides have not been reported on the common asymmetric catalysis with catalyst proline derivatives

Method used

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  • Proline sulfinamide double-chirality organic molecular catalyst and preparation method thereof
  • Proline sulfinamide double-chirality organic molecular catalyst and preparation method thereof
  • Proline sulfinamide double-chirality organic molecular catalyst and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1.( R )-N-(( S )-tert-butylsulfinyl) 2-prolinecarboxamide: under ice-water bath, add 480 mg (12 mmol, 60%) NaH to a dry 150-ml three-necked flask filled with nitrogen, add 25 ml of freshly distilled THF, rapidly injected with 1.21 g (10 mmol) of ( S)-tert-butylsulfinamide in 15 milliliters of anhydrous THF, after half an hour of reaction, slowly add 2.39 grams (10 mmol) of N-tert-butoxycarbonyl-D-proline methyl ester dropwise with a dropping funnel, drop After the addition was complete, remove the ice-water bath and react for 48 hours. Add saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate (30 ml × 3), combine the organic phases, dry with anhydrous sodium sulfate, spin off the solvent, spin dry and separate by silica gel column chromatography (petroleum ether: Ethyl acetate=3:1), afforded 2a (2.38 g) as a white solid. Yield 75%.

[0037] ( R )-N-(( R )-tert-butylsulfinyl) 2-proline carboxamide: under ice-water bath, filled wit...

Embodiment 2

[0040] Embodiment two: catalyst ( R )-N-(( S )-tert-butylsulfinyl) 2-proline carboxamide trifluoroacetate, ( R )-N-(( R )-tert-butylsulfinyl)2-prolinecarboxamide trifluoroacetate was applied to the direct asymmetric aldol condensation reaction respectively, 3a catalyst can be synthesized in high yield and high diastereoselectivity and enantioselectivity A-hydroxy ketone compound, reaction principle is as follows:

[0041]

[0042] The catalyst is:

[0043]

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Abstract

The invention relates to a proline sulfinamide double-chirality organic molecular catalyst and a preparation method thereof. The catalyst has the structural formula represented by the formula 3a or the formula 3b. According to the preparation method, tert-butylsulfinamide having opposite chirality is introduced into a proline derivative, and the proline sulfinamide double-chirality organic small-molecular catalyst having a corresponding structure and containing chiral sulfur is synthesized for the first time. The raw materials are easy to get, the operations are simple, and the yield of the synthesized catalyst reaches up to 70%. The synthesis method has the characteristics of simple operations, brief procedures, convenient post-processing and the like. The preparation method mainly utilizes combined action of proline and tert-butyl sulfinyl to induce a substrate, and thus some relatively good results are achieved; and at the same time, the preparation method also can clearly indicate that proline and tert-butylsulfinamide have leading roles in catalytic induction. Therefore, the catalyst and the preparation method have higher application value.

Description

technical field [0001] The invention relates to a bichiral organic small molecule catalyst and a preparation method thereof, in particular to a proline sulfinamide bichiral organic molecule catalyst and a preparation method thereof. Background technique [0002] Chirality is one of the basic properties of nature and closely related to life. Chirality plays an irreplaceable role in the life process. Therefore, its application involves various fields, among which chiral catalysis is particularly important in chemistry. The 2001 Nobel Prize in Chemistry was awarded to three scientists engaged in chiral chemistry, William S. Knowles and K. Barry Sharpless, and Professor Ryji Noyori. Although great progress has been made in the field of chiral catalysis, the selectivity and efficiency of catalytic reactions are still the bottleneck in this field. Therefore, the development of new chiral catalysts with high efficiency, high selectivity and environmental friendliness has become...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/04C07D207/16C07C205/45C07C201/12
Inventor 高伟麻国斌胡天泽范云鹏万文王静蒋海珍郝健
Owner SHANGHAI UNIV
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