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Chelating chiral boric acid ester and preparatio process and use thereof

A boronate, chiral technology, applied in the field of chiral compound preparation chemistry, to achieve the effects of strong oxidation resistance, high thermal stability and simple preparation process

Inactive Publication Date: 2003-08-06
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as the asymmetric reaction catalyzed by chiral boron compounds is concerned, only chiral β-amino alcohols and borazolidines generated on-site by borane are used as catalysts for asymmetric reduction of three-coordinated boron compounds; chiral four-coordinated Asymmetric reactions catalyzed by boron compounds have been rarely reported so far (hetero-Diels-Alder reaction catalyzed by dienantiopure 1,1'-binaphthol boronic acid: J.Am, Chem.Soc.1994, 116, 10520; dialkyl The asymmetric reduction catalyzed by the β-aminoalcohol derivative of borane 9-BBN: Tetrahedron, 2002, 58, 1069); while the asymmetric reaction catalyzed by chelating chiral boronic esters with one N→B bond has never reported

Method used

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  • Chelating chiral boric acid ester and preparatio process and use thereof

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Effect test

Embodiment 1

[0016] Preparation of (R)-1,1-bi-2-naphtholboronic acid-(S)-(2-pyrrolidinyl)-1,1-diphenylmethyl ester: 2.86g (10mmol)(R)- 1,1′-bi-2-naphthol and 2.4mL (1.96g, 10.08mmol) triisopropyl borate were refluxed in toluene for 6 hours and then stoichiometric (S)-(2-pyrrolidinyl)- 1,1-Diphenylmethanol, continue to reflux for 6 hours, cool down, evaporate (80-90°C) toluene and isopropanol under reduced pressure with a water pump, and treat the residue with ethanol to obtain (R)-linked- 2-Naphtholboronic acid-(S)-(2-pyrrolidinyl)-1,1-diphenylmethyl ester.

Embodiment 2

[0018] The preparation of catechol boric acid (S)-proline anhydride: similar to Example 1, catechol and triisopropyl borate were refluxed in benzene and added stoichiometric (S)-proline after 6 hours to continue After reflux for 6 hours, an oily substance was generated and solidified after cooling. The solid was separated and crystallized from methanol to give 61% catecholboronic acid (S)-proline anhydride, m.p. 196-198°C.

Embodiment 3

[0020] Preparation of (S)-1,1'-bi-2-naphthol boronic acid-quinalidine anhydride: (S)-1,1'-bi-2-naphthol (2.86g, 10mmol) and 0.92M BH 3 THF (12ml, 11mmol) solution was reacted at room temperature in THF for 2 hours; the solvent and excess borane were evaporated under reduced pressure; anhydrous quinaldinic acid (1.75 grams, 10mmol) and benzene (40mL) were added, stirred at room temperature for 0.5 hours After that, it was refluxed for another 2 hours; (S)-bi-2-naphtholboronic acid-quinalidine anhydride was almost quantitatively obtained.

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Abstract

The present invention relates to a chelating chiral boric acid ester, its preparation method and application. Said invention provides its structure general formula, and it is made up by glycol or diphenol, alkamine or amino acid and boron compound and making them produce reaction. It is characterized by that in the above-mentioned glycol, diphenol, alkamine or amino acid at least one of them is chiral compound. Said invented chelating chiral boric acid ester as catalyst possesses high thermal stability, hydrolysis stability and optical stability, and has strong oxidation resistance and acidolysis resistance. It is low in cost, and has the extensive application in asymmetric catalytic synthesis process.

Description

technical field [0001] The invention relates to a novel class of chiral catalyst chelating chiral borates synthesized asymmetrically, a preparation method and application thereof. It belongs to the field of chiral compound preparation chemistry. Background technique [0002] The preparation of photoactive compounds by asymmetric catalysis has always been a hot research topic for synthetic chemists. Most of the chiral catalysts used in asymmetric catalysis are chiral complexes of transition metals. Chiral compounds of main group elements are relatively less used as catalysts for asymmetric reactions. In terms of asymmetric reactions catalyzed by chiral boron compounds, only chiral β-aminoalcohols and borane-generated borazolidines are used as catalysts for asymmetric reduction of three-coordinated boron compounds; chiral four-coordinated Asymmetric reactions catalyzed by boron compounds have been rarely reported so far (hetero-Diels-Alder reaction catalyzed by bis-enantiop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F5/04
Inventor 单自兴刘德军褚运波
Owner WUHAN UNIV
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