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Chiral hexahydroxy n-heterocyclic carbine precursor compound as well as preparation method and application thereof

A technology for nitrogen heterocyclic carbene and precursor compounds, which is applied in the field of preparation of chiral six-membered nitrogen heterocyclic carbene precursor compounds, and can solve the problem of less research on chiral six-membered ring nitrogen heterocyclic carbene metal complexes

Inactive Publication Date: 2014-05-07
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The above studies mainly focus on chiral five-membered ring azacarbene and its metal compounds which are easy to synthesize and have stable properties, but there are relatively few studies on chiral six-membered ring azacarbene and its metal complexes.

Method used

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  • Chiral hexahydroxy n-heterocyclic carbine precursor compound as well as preparation method and application thereof
  • Chiral hexahydroxy n-heterocyclic carbine precursor compound as well as preparation method and application thereof
  • Chiral hexahydroxy n-heterocyclic carbine precursor compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Preparation and characterization of compound I-1:

[0084]

[0085] Dissolve 4.0g (20.3mmol) of compound I' and 3.84g of tert-butylsulfinamide in 100mlTHF, add 40mmol of tetraisopropyl titanate, monitor the reaction progress with TLC, use general method 1 to react, and heat at 86°C Stir for 12hr, after the reaction finishes, the reaction solution is poured into NaHCO 3 (200ml) solution, a large number of yellow solids precipitated, suction filtered, the solution was extracted three times with ethyl acetate (300ml), and the organic phase was washed with anhydrous Na 2 SO 4 Drying, suction filtration, spin-drying, and column chromatography separation (petroleum ether: ethyl acetate = 10:1) yielded 5.4 g of compound I-1 with a yield of 89% and a melting point of 140-142°C; 1 H NMR (400MHz, CDCl 3 ,ppm)δ:7.49(s,3H),7.24-7.26(m,2H),7.29-7.13(m,3H),6.73-6.91(m,4H),6.51(s,4H),1.28(s, 9H); 13 C NMR (100MHz, DMSO-d 6 ,δ):156.3,141.5,128.5,128.1,128.0,127.1,126.2,111.5,5...

Embodiment 2

[0087] Preparation and characterization of compound I-2:

[0088]

[0089] The preparation conditions are the same as in Example 1, the yield is 88%, and the melting point is 138~140°C; 1 H NMR (400MHz, CDCl 3 ,ppm)δ:7.50(s,3H),7.26(s,1H),7.16(d,J=7.6Hz,1H),6.84(s,1H),6.71(d,J=8.8Hz,1H), 1.27(s,9H); 13 C NMR (100MHz, CDCl 3 ,δ):154.3,141.8,128.5,128.1,128.0,127.1,126.2,111.3,57.5,55.8,22.7; MS(ESI-TOF)m / z:335.2[M+H] + .

Embodiment 3

[0091] Preparation and characterization of compound I-3:

[0092]

[0093] The preparation conditions are the same as in Example 1, the yield is 86%, and the melting point is 136~138° C.; 1 H NMR (400MHz, CDCl 3 ,ppm)δ:7.51-7.53(m,1H),7.15-7.30(m,3H),6.71(d,J=8.8Hz,1H),1.27(s,9H); 13 C NMR (100MHz, CDCl 3 ,δ):152.1,141.9,128.6,128.3,128.1,127.5,126.4,111.6,57.5,55.8,22.8; MS(ESI-TOF)m / z:353.1[M+H] + .

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Abstract

The invention relates to the field of organic synthesis, and particularly relates to a preparation method and an application of a chiral hexahydroxy n-heterocyclic carbine precursor compound. The compound has a structure as shown in a formula (V) in descriptions. The chiral hexahydroxy n-heterocyclic carbine precursor compound can be used for catalyzing multiple chiral reactions such as an addition reaction of unsaturated esters, alpha,beta-unsaturated imine and diborane pinacol borate, or a condensation reaction of aldehyde and boric acid compounds or a reduction reaction of ketone and has relatively good catalytic efficiency and enantioselectivity. (imgfile='DDA0000462319780000011.T'IF wi='392 he='496' / ).

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method and application of a chiral six-membered nitrogen heterocyclic carbene precursor compound. Background technique [0002] In 1991, Arduengo et al. isolated and characterized N-heterocyclic carbene (NHCs) monomers for the first time, and then there was a leap in the development of N-heterocyclic carbene (NHCs) chemistry. Since the reaction catalyzed by N-heterocyclic carbene has the advantages of no metal participation, low price, and relatively loose environmental requirements, it has received more and more attention, and its unique catalytic performance has also provided people with a search for new catalysts with good performance. opened up new horizons. In addition, since N-heterocyclic carbene is a strong δ-electron donor, it can be complexed with almost all transition metals to obtain N-heterocyclic carbene metal complexes. These organic complexes can ca...

Claims

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Application Information

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IPC IPC(8): C07D239/74B01J31/02C07F5/04C07C33/24C07C29/44C07C33/20C07C29/143
CPCB01J31/0244B01J2231/482B01J2231/643C07C29/143C07C29/44C07D239/74C07F5/04C07C33/24C07C33/20
Inventor 孙智华黄立梁曹泳
Owner SHANGHAI UNIV OF ENG SCI
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