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1, 2-diol ester compound and preparation method thereof

A compound, C2-C10 technology, applied in the field of 1,2-diol ester compounds and their preparation, can solve the problems of poor functional group compatibility, poor enantioselectivity, poor substrate universality and the like

Active Publication Date: 2022-03-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the defects of poor substrate universality, poor functional group compatibility and poor enantioselectivity of the existing non-active terminal asymmetric double oxidation reaction, and provide a 1,2-diol Esters and their preparation methods

Method used

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  • 1, 2-diol ester compound and preparation method thereof
  • 1, 2-diol ester compound and preparation method thereof
  • 1, 2-diol ester compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0262] Example 1 Preparation of 1,2-diol esters

[0263]

[0264] General procedure 1: In a 10mL reaction tube, oxazoline ligand (20mg, 0.075mmol, 15mol%), Pd(OAc) 2 (11.2mg, 0.05mmol, 10mol%) and PhI(OAc) 2 (193.3mg, 0.6mmol, 1.0equiv) under the protection of propylene or 1-butene, add formula III-1 compound (1.25mmol, 2.5equiv) and Et 2 O (0.25 mL). The reaction was stirred at -10°C for 96 hours. After the reaction, it was diluted with 10 mL of ethyl acetate and washed with water (10 mL×3). The organic phase was washed with anhydrous MgSO 4 After drying and filtering, the filtrate was concentrated and separated by flash column chromatography (petroleum ether / ethyl acetate) to obtain the target product.

[0265] General operation step 2: in 10mL reaction tube, oxazoline ligand (20mg, 0.075mmol, 15mol%), Pd(OAc) 2 (11.2mg, 0.05mmol, 10mol%) and PhI(OAc) 2 (193.3mg, 0.6mmol, 1.2equiv) under argon protection, add formula III-1 compound (1.25mmol, 2.5equiv), Et 2 O (0....

Embodiment 2

[0474] The influence of embodiment 2 oxidant on double oxidation reaction

[0475] According to the method of operation 2 in embodiment 1, adopt following oxidant, reaction result is as follows.

[0476]

Embodiment 3

[0477] The influence of embodiment 3 oxazoline ligands on double oxidation reaction

[0478]

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Abstract

The invention discloses a 1, 2-diol ester compound and a preparation method thereof. The invention provides a preparation method of a compound containing a fragment A. The preparation method comprises the following step: in the presence of a palladium catalyst, an oxazoline ligand and an oxidizing agent, carrying out a reaction as shown in the specification on a compound containing a fragment II and a compound as shown in a formula III to obtain the compound containing the fragment A, the preparation method disclosed by the invention is novel, and further, the preparation method has the advantages of good enantioselectivity, high yield, wide substrate universality and good functional group compatibility.

Description

technical field [0001] The invention relates to a 1,2-diol ester compound and a preparation method thereof. Background technique [0002] Optically active 1,2-diol ester compounds and their derivatives such as chiral 1,2-diol widely exist in pharmaceutical molecules and fine chemical products, and are widely used synthetic building blocks in organic synthesis. Therefore, it is of great significance to develop methods for synthesizing these compounds. It is the most direct and efficient method to synthesize these compounds by asymmetric double oxidation of cheap and readily available alkenes as raw materials. Methods for the synthesis of such compounds have been extensively studied in recent decades. Among them, the metal osmium-catalyzed double oxidation reaction developed by the Shapless group is currently the most frequently used and widely used method for the synthesis of chiral 1,2-diols (Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B.Chem.Rev.1994, 94, 2483.). Howe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07C67/055C07C69/16C07C69/63C07C253/30C07C255/14C07C69/18C07C69/78C07C201/12C07C205/40C07C315/04C07C317/18C07C303/30C07C309/73C07F7/18C07C69/675C07C205/37C07F5/02C07C69/732C07C303/40C07C311/17C07D333/32C07D307/68C07D307/85C07D333/68C07D209/42C07C69/21C07C69/618C07C67/31C07C67/29C07C69/82C07C69/92C07D311/52C07D311/16C07D313/12C07D307/80C07C69/712C07J1/00
CPCC07D209/48C07C67/055C07C253/30C07C201/12C07C315/04C07C303/30C07F7/1804C07F7/1892C07F5/025C07C303/40C07D333/32C07D307/68C07D307/85C07D333/68C07D209/42C07C67/31C07C67/29C07D311/52C07D311/16C07D313/12C07D307/80C07J1/0059C07J1/0025C07B2200/13C07C2601/14C07C2531/22C07C2531/18C07C69/16C07C69/63C07C255/14C07C69/18C07C69/78C07C205/40C07C317/18C07C309/73C07C69/675C07C205/37C07C69/732C07C311/17C07C69/21C07C69/618C07C69/82C07C69/92C07C69/712Y02P20/55
Inventor 刘国生田兵陈品红
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI