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A kind of biphenyl axial chiral compound and its synthesis method

A synthesis method and axial chirality technology, applied in the field of biphenyl-based axial chiral compounds and their synthesis, can solve the problems of long development time and application limitations, and achieve the effect of excellent performance and excellent stereoselectivity.

Active Publication Date: 2021-01-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Long development time but limited application

Method used

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  • A kind of biphenyl axial chiral compound and its synthesis method
  • A kind of biphenyl axial chiral compound and its synthesis method
  • A kind of biphenyl axial chiral compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of (R)-3a:

[0029]Under nitrogen, substrate 1a (58.5 mg, 0.25 mmol) and substrate 2a (17.9 mg, 0.1 mmol) were dissolved in a mixed solvent of 1 ml N-methylpyrrolidone and 0.5 ml tert-butanol, and catalyst C1 ( 7.4mg, 20mol%), oxidant B (142mg, 0.35mmol) and organic base 1,4-diazabicyclo[2.2.2]octane (DABCO, 6mg, 0.05mmol)) were stirred at a temperature of 60°C 12 hours. After the reaction was complete, the mixture was extracted by adding ethyl acetate and saturated ammonium chloride solution, washed with water, washed with saturated brine, dried, evaporated under reduced pressure to remove the solvent, and separated by column chromatography to obtain the product 3a.

[0030] 133.4, 132.7, 129.4, 128.9, 128.2, 127.9, 127.9, 127.6, 127.3, 126.8, 126.6, 124.4, 20.9ppm.

Embodiment 2

[0031] Embodiment 2: the synthesis of (R)-3b:

[0032] Replace substrate 1 with R 1 =4-Cl-Ph, refer to Example 1 for other experimental operations.

[0033] 127.7, 126.9, 126.3, 124.4, 20.9ppm.

Embodiment 3

[0034] Embodiment 3: the synthesis of (R)-3c:

[0035] Replace substrate 1 with R 1 =4-Br-Ph, refer to Example 1 for the remaining experimental operations.

[0036] ppm.

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Abstract

The invention discloses a biphenyl axial chiral compound and a synthesis method thereof. The biphenyl axial chiral compound has the following structure (being defined as in the specification), whereinR1 is an aromatic substituent group, and includes ortho-position, meta-position, para orientation, electron-giving, electron-withdrawing and halogen-substituted phenyl; R2 is an aromatic substituentgroup, and includes ortho-position, meta-position, para orientation, electron-giving, electron-withdrawing and halogen-substituted phenyl; R3 is an aromatic group or a methyl substituent group; and R4is an ortho-position electron-withdrawing group monosubstituted or polysubstituted group. According to the biphenyl axial chiral compound and the synthesis method thereof, a method for formation of atropisomer arene by [4+2] cycloaddition among n-heterocyclic carbene small organic molecule catalytic molecules is established, the biphenyl axial chiral compound is prepared, starting materials are all easy to prepare, activation of the substrate remote reaction site is realized, the biphenyl axial chiral compound is constructed in one step, and the stereoselectivity is excellent; and the prepared biphenyl axial chiral compound can be easily transformed into axial chiral small organic molecule ligands, and broad application prospects in catalysis and ligands are achieved.

Description

technical field [0001] The invention relates to a biphenyl axial chiral compound and a synthesis method thereof. Background technique [0002] Atropisomer aromatic compounds are special structures with restricted rotation single bonds, which widely exist in natural products, drug molecules, catalysts and functional molecules (Nat.Prod.Rep.2015,32,1562-1583; J. Med. Chem. 2011, 54, 7005-7022; Chem. Rev. 2005, 105, 857-897). As people pay more and more attention to this class of compounds, the development of new methods for the synthesis of axichiral molecules is also of increasing research value. So far, the most advanced methods for the synthesis of atropisomer aromatics are summarized in figure 1 Among them, it mainly includes the asymmetric modification of aromatic hydrocarbons by metal-catalyzed cross-coupling (Coord. Electrophilic substitution reaction (J. Am.Chem.Soc.2015,137,15062-15065; Angew.Chem.Int.Ed.2017,56,116-121; Nat.Chem.2018,10,58-64; Nat. Catal.2019,2,3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B53/00C07C205/06C07C201/12C07C205/12C07C205/11C07C205/35C07D213/26C07D333/12C07D213/61C07C253/30C07C255/50C07F9/53C07C211/45C07C275/30C07C335/16C07C233/56C07C47/546C07F9/50
CPCC07B53/00C07B2200/07C07C47/546C07C205/06C07C205/11C07C205/12C07C205/35C07C211/45C07C233/56C07C255/50C07C275/30C07C335/16C07D213/26C07D213/61C07D333/12C07F9/5022C07F9/5054C07F9/5325
Inventor 朱庭顺许可李文长朱劭恒
Owner SUN YAT SEN UNIV