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Use of chiral oxazoline

A chiral oxazoline, oxazoline technology, applied in asymmetric synthesis, hydrogen cyanide addition preparation, organic compound/hydride/coordination complex catalyst, etc., can solve problems such as low efficiency and complicated operation

Inactive Publication Date: 2008-01-09
HEFEI UNIV OF TECH
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Problems solved by technology

Although chiral cyanohydrins can be separated from racemat

Method used

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  • Use of chiral oxazoline
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  • Use of chiral oxazoline

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[0024] 1. Preparation of Catalysts 1a-1e

[0025] Now piperidine oxazoline, pyrrole oxazoline and ethyl zinc (ZnEt 2 ) as an example, non-limiting embodiments are described as follows:

[0026] When R is isobutyl, isopropyl, phenyl and benzyl, the catalyst prepared by piperidine oxazoline and ethyl zinc is respectively called catalyst 1a, 1b, 1c and 1d; pyrrole oxazoline and ethyl zinc are prepared The catalyst is called catalyst 1e.

[0027] 1a-1d: 1-[2-(4S)-4-isobutyl-4,5-dihydro-2-oxazolinyl-ethyl]piperidine, 1-[2-(4S)-4- Isopropyl-4,5-dihydro-2-oxazolinyl-ethyl]piperidine, 1-[2-(4S)-4-phenyl-4,5-dihydro-2-oxazoline Base-ethyl]piperidine, 1-[2-(4S)-4-benzyl-4,5-dihydro-2-oxazolinyl-ethyl]piperidine each 0.15g, respectively dissolved in THF solvent In, add ZnEt 2 0.4ml, reacted at room temperature for 24 hours, respectively prepared catalysts 1a-1d.

[0028] 1e: Preparation of 1-[2-(4S)-4-isopropyl-4,5-dihydro-2-oxazolinyl-ethyl]tetrahydropyrrole-zinc complex

[0029...

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Abstract

The present invention is use of chiral oxazolinyl. The complex comprising 1-[2-(4S)-4-R-4.5-dihydro-2- oxazolinyl-ethyl]piperidine or 1-[2-(4S)-4-isopropyl-4.5- dihydro-2-oxazolinyl-ethyl] tetrahydropyrrole, and the chloride or diethylate of bivalent metal Zn, Cu, La or Sm is used as the chiral catalyst for the addition reaction between aromatic aldehyde, substituted aromatic aldehyde or butyl aldehyde and cyanide or nitrile to prepare chiral target product. In the addition reaction of para aromatic aldehyde, R-form as main target product may be obtained in the conversion rate higher than 80 %, and ee % greater than 97 %; and in other addition reaction, S-form as main target product may be obtained in the conversion rate higher than 80 %, and ee % greater than 99 %.

Description

1. Technical field [0001] The present invention relates to a new use of a known compound, in particular a use of a chiral oxazoline. 2. Background technology [0002] The complexes of chiral oxazoline and rare earth metals are used in Diels-Alder diene cycloaddition reaction, Michael condensation reaction and Friedel-Crafts condensation Reaction, Aldol (aldol) condensation reaction and many other reactions showed good asymmetric catalytic activity and high enantioselectivity. [0003] The applicant synthesized a new type of chiral oxazoline 1-[2-(4S)-4-R-4.5-dihydro-2-oxazoline-ethyl]piperidine, and applied for a Chinese invention patent. Publication number CN1939911A. [0004] Cyanohydrin compounds are important intermediates in organic synthesis, especially chiral aryl cyanohydrin is an important pharmaceutical intermediate. Therefore, the addition reaction of carbonyl groups, especially aromatic aldehydes, with cyanides or nitriles (nitrile silicidation) has been exten...

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Application Information

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IPC IPC(8): B01J31/22B01J31/26C07C253/08C07B53/00
Inventor 罗梅
Owner HEFEI UNIV OF TECH
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