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Spirocyclophophorous amine

A technology of spirocyclic phosphoramidites and right-handed spirocyclic phosphoramidites, which is applied in the field of synthesis of chiral ligand compounds, can solve problems such as poor stability and inconvenience, and achieve high stereoselective effects

Inactive Publication Date: 2002-04-03
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some of these ligands have high selectivity, they all have a fatal weakness, that is, poor stability and must be used in a nitrogen atmosphere, which is extremely inconvenient

Method used

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  • Spirocyclophophorous amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of (±)-O, O'-[7,7'-(1,1'-spirodihydroindene)]-N,N-dimethylphosphoramidite

[0017] In a 250ml reaction bottle, add 2g (8mmol) (±)-spirocyclic diphenol, 2ml (9mmol) hexamethylphosphoramidite, 20ml anhydrous toluene, and react in a nitrogen stream at 100°C for 2 hours, TLC tracking The response is complete. The resulting reaction solution was subjected to silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1:16) to obtain white crystals, (±)-O,O'-[7,7'-(1,1'-spiro Dihydroindane)]-N,N-dimethylphosphoramidite 2.37g, yield 92%, melting point 117-118°C.

[0018] 1 H NMR (300MHz, CDCl 3 ): δ=7.24-6.98(m, 4H), 6.93(d, J=8.1Hz, 1H), 6.64(d, J=8.1Hz, 1H), 3.13-3.01(m, 2H), 2.82(dd, J=16.2, 8.1 Hz, 2H), 2.34 (s, 3H), 2.31 (s, 3H), 2.30-2.18 (m, 2H), 2.08-1.80 (m, 2H). 31 P NMR (CDCl 3 ): δ=124.96. Elemental analysis (theoretical value), C 19 h 20 NO 2 P: C69.95 (70.13); H6.06 (6.21); N4.40 (4.30).

Embodiment 2

[0020] Preparation of (R)-O, O'-[7,7'-(1,1'-spirodihydroindene)]-N,N-dimethylphosphoramidite

[0021] Substitute (±)-spirocyclic diphenol in Example 1 with (R)-spirocyclic diphenol, the preparation method, chemical structural formula, spectral data and elemental analysis are the same as in Example 1, with a melting point of 84-85°C, [α] 20 D =+525 (c=1.14×10 -2 , CHCl 3 ).

Embodiment 3

[0023] Preparation of (S)-O, O'-[7,7'-(1,1'-spirodihydroindene)-N,N,N-dimethylphosphoramidite

[0024] The (±)-spirocyclic diphenol in Example 1 is replaced with (S)-spirocyclic diphenol, the preparation method, chemical structural formula, spectral data and elemental analysis are the same as in Example 1, with a melting point of 84.5-85.5°C, [α] 20 D =-519 (c=0.92×10 -2 , CHCl 3 )

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Abstract

A spirocyclic phosphorous amide is prepared though reaction of spirocyclicdiphenols on substituted phosphorous amide, and features that it has two mutamers: dextro-and levo-spirocyclicphosphorous amides. It can be used for asymmetric catalytic hydrogenating reaction with very high stereo-selectivity (more than 99% of e.e. value).

Description

technical field [0001] The invention belongs to the synthesis of chiral ligand compounds, in particular to the preparation of a spirocyclic phosphoramidite with a C2 symmetry axis. Background technique [0002] α-Amino acids are an important class of compounds, and the polypeptides (proteins) formed by amide bonds play an extremely important role in living organisms. Through deep processing, compounds with different configurations can be obtained, and these compounds have important uses in biology and pharmacy. Chiral α-amino acids can also be used as chiral inducers for chiral synthesis. Therefore, the chiral synthesis of α-amino acids has always been the focus of organic synthesis. The catalytic hydrogenation of dehydroamino acid is the earliest method developed. The dehydroamino acid derivative is used as the substrate, and the hydrogenation reaction occurs in the presence of a chiral catalyst to obtain an optically active amino acid produ...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07C51/36C07C55/02C07C67/303C07C69/34C07C211/24C07C227/16C07C229/06C07F9/6571
Inventor 周其林付煜谢建华王立新周海
Owner NANKAI UNIV
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