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Preparation method of optically active beta-hydroxy ketone

A photoactive, hydroxy ketone technology, applied in the field of preparing photoactive β-hydroxy ketone, can solve the problems of high preparation cost, low catalytic efficiency, complicated preparation procedures, etc., and achieves simple and easy to obtain raw materials, low preparation cost and simple process Effect

Inactive Publication Date: 2007-08-15
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the chiral catalysts used in the above-mentioned aldol addition reactions, except for proline, mostly have disadvantages such as complicated preparation procedures and expensive preparation costs; the application range of proline is also limited, especially for aromatic aldehydes and The catalytic efficiency of the direct aldol addition reaction of ketones is relatively low

Method used

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  • Preparation method of optically active beta-hydroxy ketone

Examples

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Effect test

Embodiment l

[0019] This example provides a representative procedure that will be used in the following examples: In a Schlenk test tube equipped with a stir bar and methyl ketone or monosubstituted methyl ketone or cyclic ketone, add There are 0.01-1.50 equivalents of chiral spiro borate catalyst, stirred at -25 to 80°C for 15 minutes, and then added aldehyde, the molar ratio of aldehyde and methyl ketone or monosubstituted methyl ketone or cyclic ketone is 1.00:1.00~10.0 , and continue to stir at this temperature for 10-100h. Add 0.1-10.0 equivalents of saturated NH 4 Cl aqueous solution or dilute hydrochloric acid or dilute sulfuric acid solution, stirred, extracted, combined organic phase, dried (anhydrous Na 2 SO 4 ), after concentration, the catalyst crystals were left to separate out, separated, and the mother liquor was subjected to flash column chromatography on silica gel to obtain photoactive β-hydroxy ketones.

[0020] Such as: the addition of acetone and benzaldehyde, the s...

Embodiment 2

[0022] According to the operating procedure of Example 1, excess acetone and benzaldehyde were added at 20°C with 0.3 equivalent catalyst, and extracted with ether to obtain (R)-4-hydroxyl-4-phenyl-2-butanone, [α ] D 25 =+43.02 (c=0.30, inCHCl3 ), 11% yield, 70% ee

Embodiment 3

[0024] According to the operating steps of Example 1, acetone and benzaldehyde were added in THF at -15°C with 0.3 equivalent catalysts to obtain (R)-4-hydroxyl-4-phenyl-2-butanone, [α] D 25 =+50.59(0.09, in CHCl 3 ), 64% yield, 83% ee.

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Abstract

The present invention relates to a method for preparing photoactive beta-alcohol ketone. It is characterized by that in the presence of chiral spiroborate with O3BN skeleton, under the moderate condition it can make methyl ketone or single-substituted methyl ketone or cyclic ketone p-aldehyde implement direct aldol addition reaction so as to obtain the invented photoactive beta-alcohol ketone.

Description

technical field [0001] The invention relates to a method for preparing photoactive β-hydroxy ketone through catalyzed direct asymmetric aldol (aldo1) addition with high enantioselectivity, and belongs to the field of chiral compound preparation chemistry. Background technique [0002] Photoactive β-hydroxyketones are important chiral compounds with two typical functional groups, and they are widely used in the preparation of chiral drugs and natural products. [0003] Aldol addition reaction is an important method to prepare photoactive β-hydroxy ketones. This method is divided into two types: Mukaiyama type aldol reaction and direct aldol reaction. The Mukaiyama type aldol reaction is to convert a relatively poorly reactive ketone into a highly reactive enolate by reacting with a metal reagent, a silicon reagent or a boron reagent in advance, and then add it to an aldehyde in a chiral environment and then hydrolyze it to obtain a chiral β -Hydroxyketones. This method requ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/64
Inventor 单自兴周炎
Owner WUHAN UNIV
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