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Preparation method of addition product of aldehyde and nitroolefin

A technology of nitroolefins and addition products, which is applied in the field of preparation of addition products, can solve the problems of complex catalyst preparation, difficulty in realizing industrialization or even gram-level production, and low catalytic efficiency, and achieve simple structure and easy large-scale production , high catalytic efficiency

Active Publication Date: 2013-02-27
UNIV OF SCI & TECH OF CHINA
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Problems solved by technology

[0004] At present, the organic small molecule catalysts required to obtain highly enantioselective products through the asymmetric Michael addition of aldehydes and nitroalkenes are relatively complex and require multi-step reactions to prepare, and it is difficult to achieve industrialization or even gram-level production, such as Y .Hayashi et al obtained prolinol by reducing the proline molecule, and then substituted it with a diphenyl group, and the obtained product was further prepared through a methyl silylation reaction to prepare an organic small molecule catalyst for aldehyde p-nitro The asymmetric Michael addition reaction of alkenes, the preparation of the catalyst is relatively complicated, and the catalytic efficiency is low

Method used

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  • Preparation method of addition product of aldehyde and nitroolefin
  • Preparation method of addition product of aldehyde and nitroolefin
  • Preparation method of addition product of aldehyde and nitroolefin

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preparation example Construction

[0047] The invention provides a kind of preparation method of the addition product of aldehyde and nitroalkene, comprises the following steps:

[0048] a) The nitroalkene with the structure of formula (I) and the aldehyde with the structure of formula (II) undergo an addition reaction under the action of (S)-lithium proline or (R)-lithium proline and a solvent to obtain Addition products as shown in formula (III) or formula (IV);

[0049] Formula (I); Formula (II);

[0050] Formula (III); Formula (IV);

[0051] Among them, R 1 is an alkyl group, a substituted alkyl group, an aromatic group or a substituted aromatic group, R 2 is an alkyl group, a substituted alkyl group, an aromatic group or a substituted aromatic group.

[0052] The present invention uses nitroalkenes with formula (I) and aldehydes with formula (II) as raw materials, and the addition occurs under the condition of (S)-lithium proline or (R)-lithium proline as a catalyst. reaction to obtain the add...

Embodiment 1

[0077] Take 2.3g of L-proline and add it to a 50mL round bottom flask, add 20mL of methanol, dissolve under stirring at room temperature, then add 840mg of lithium hydroxide monohydrate, stir at room temperature for 4 hours, and remove the solvent by rotary evaporation to obtain L-proline Lithium Oxide.

Embodiment 2

[0079] Take 2.3g of D-proline and add it into a 50mL round bottom flask, add 20mL of methanol, dissolve under stirring at room temperature, then add 840mg of lithium hydroxide monohydrate, and stir at room temperature for 4 hours. The solvent was removed by rotary evaporation to obtain lithium D-proline.

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Abstract

The invention provides a preparation method of addition product of aldehyde and nitroolefin. (S)-proline lithium or (R)-proline lithium is used as a chiral catalyst to katalyze the asymmetric Michael addition reaction between aldehyde and nitroolefin. The (S)-proline lithium or (R)-proline lithium has high catalytic efficiency; and the obtained addition product of aldehyde and nitroolefin has the advantages of high stereoselectivity and simple structure, is cheap and accessible, and can easily implement large-scale production.

Description

technical field [0001] The invention relates to the technical field of addition reaction of aldehydes and nitroolefins, in particular to a preparation method of an addition product of aldehydes and nitroolefins. Background technique [0002] Michael addition reaction is the conjugated addition reaction of nucleophiles to α,β-unsaturated carbonyl compounds, and is the most commonly used method to construct carbon-carbon bonds. In the Michael addition reaction, on the one hand, because the carbon atom at the β position in the conjugated system is converted from the original sp2 hybridized carbon atom to the sp3 hybridized carbon atom, this hybridization can occur enantioselectively, is The basis for the preparation of asymmetric products; on the other hand, because the Michael addition reaction can provide intermediates for many useful organic compounds and natural products through carbon-carbon bond construction from simple and easy-to-obtain raw materials, the Michael additi...

Claims

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Application Information

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IPC IPC(8): C07B53/00C07C205/44C07C201/12C07D307/46
Inventor 汪志勇徐坤查正根
Owner UNIV OF SCI & TECH OF CHINA
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