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Axially-chiral indole-naphthalene compounds and preparation method thereof

A compound, axial chiral technology, applied in the field of organic synthetic chemistry, can solve limited problems, achieve mild reaction conditions, high yield, and broaden the scope of application

Active Publication Date: 2019-11-15
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite these methods, they are still very limited, so there is an urgent need to develop new methods and strategies for the synthesis of axially chiral indole-naphthalene and indole-benzene compounds

Method used

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  • Axially-chiral indole-naphthalene compounds and preparation method thereof
  • Axially-chiral indole-naphthalene compounds and preparation method thereof
  • Axially-chiral indole-naphthalene compounds and preparation method thereof

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Embodiment 1

[0029] Embodiment 1: in the mixed solvent (v / v=1:4) of 1 milliliter 1,1,2,2-tetrachloroethane and p-xylene, add 0.1 mmol of formula 7a compound and 0.12 mmol of formula Compound 8a as reactant, 100 mg Molecular sieves are used as additives, 0.01 mmol of chiral phosphoric acid (i.e. the compound of formula 6) is used as a catalyst, reacted at 25 ° C for 12 hours, TLC traced the reaction to the end, and filtered to remove Molecular sieves, wash the filter cake with ethyl acetate, and separate the obtained filtrate through silica gel column chromatography (the eluent is a mixed solution with a volume ratio of petroleum ether and ethyl acetate of 10:1) after concentration to obtain the axial chiral indole Indole-naphthalene 9aa, white solid.

[0030] The structural characterization data of product 9aa in Example 1 are as follows:

[0031] m.p.128-129°C; [α] D 20 =-14.5 (c 0.64, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ8.24(s,1H),7.78–7.70(m,2H),7.37(d,J=8.1Hz,1H),7.28(s,2H),7....

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Abstract

The invention discloses axially-chiral indole-naphthalene compounds and a preparation method thereof. The axially-chiral indole-naphthalene compounds have a chemical structure represented by a formula9 shown in the description; and the method comprises the following steps: a compound represented by a formula 7 and a compound represented by a formula 8 are used as reaction raw materials, a mixed solution of 1,1,2,2-tetrachloroethane and p-xylene is used as a solvent, a molecular sieve is added, a reaction is performed under stirring under the action of a chiral phosphoric acid catalyst, the reaction is tracked by TLC until the reaction is completed, filtration is performed, concentration is performed, purification is performed, and therefore one compound is obtained. The method for preparing the axially-chiral indole-naphthalene compounds provided by the invention is an asymmetric addition reaction under catalysis of organic small molecules, starts from the racemic raw material to construct the axially-chiral indole-naphthalene structure in one step, and has the advantages of simple and convenient operation, mild reaction conditions and economical easily-available raw materials, and the prepared axially-chiral indole-naphthalene compounds have high optical purity; and the axially-chiral indole-naphthalene compounds prepared by the method are expected to be widely used in the field of asymmetric catalysis.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry and relates to an axial chiral biaryl compound, in particular to an axial chiral indole-naphthalene compound and a preparation method thereof. Background technique [0002] Axial chiral indole-naphthalene compounds can be used as small organic molecule catalysts to catalyze organic chemical reactions. For example, the document Angew.Chem.Int.Ed.2017,56,116 reported that this type of compound can be used as an organophosphine catalyst to catalyze the asymmetric [3+2] cyclization reaction of allenes and imines; document J.Org.Chem.2018 ,83,10060 reported that this type of compound can be used as an organophosphine catalyst to catalyze the [4+1] cyclization reaction of o-methylenebenzoquinone and Morita-Baylis-Hillman ester; literature Chem.Sci.2019,2019,10,6777 It is reported that these compounds can be used as chiral phosphine ligands to catalyze the asymmetric allylation of malonate. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12B01J31/02
CPCB01J31/0258C07B2200/07C07D209/12
Inventor 石枫张宇辰蒋飞陈科伟
Owner XUZHOU NORMAL UNIVERSITY
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