Chiral indolo-oxa seven-membered ring compound and synthesis method thereof
A synthesis method, a seven-membered ring technology, applied in the directions of organic chemistry methods, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve harsh reaction conditions, low enantioselectivity, and error-prone Operation and other problems, to achieve the effect of mild reaction process, high enantioselectivity and high enantioselectivity
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Embodiment 1
[0029] The synthetic route of the chiral indolooxa seven-membered ring compound 3aa is shown below:
[0030] In above-mentioned reaction, catalyst chiral phosphoric acid structural formula is as follows:
[0031]
[0032] In 1 ml of mesitylene, 0.1 mmol of 2,3-disubstituted indolemethanol derivative 1a and 0.12 mmol of 2-naphthol compound 2a were added as reactants, 0.01 mmol of chiral phosphoric acid (that is, formula 4 compound) as a catalyst, the reaction was stirred at room temperature for 12 hours, the reaction was followed by TLC to the end, and separated by silica gel column chromatography (the eluent was a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain the hand. Sexual indolooxa seven-membered ring compound 3aa.
[0033] The structural characterization data of product 3aa in Example 1 are as follows:
[0034] Yield: 90% (46.3 mg); white solid; melting point: 250.1-251.0°C; [α] D 20 =+97.8(c=0.42, CHCl 3 ); 1 H NMR (4...
Embodiment 2-8
[0036] The reaction synthesis route is as follows:
[0037] Reaction raw materials and productive rate are as shown in Table 1:
[0038] Table 1 * Reaction raw materials and productive rate of embodiment 2-8
[0039]
[0040] *0.1 mmol of the compound of formula 1 and 0.12 mmol of the compound of formula 2a as reactants, 0.01 mmol of the compound of formula 4 as catalyst, and 1 ml of mesitylene as solvent.
Embodiment 9-17
[0042] The reaction synthesis route is as follows:
[0043] Reaction raw materials and productive rate are as shown in table 2:
[0044] Table 2 * Reaction Materials and Yields of Examples 19-24
[0045]
[0046]*0.1 mmol of compound of formula 1a and 0.12 mmol of compound of formula 2 as reactants, 0.01 mmol of compound of formula 4 as catalyst, and 1 ml of mesitylene as solvent.
[0047] As can be seen from Table 1 and Table 2, the method of the present invention can not only realize the synthesis of chiral indolooxa seven-membered ring compounds with high atom economy and environmental friendliness, but also can achieve the synthesis of chiral indolooxa seven-membered ring compounds with excellent yield, high enantio The expected chiral indolooxa seven-membered ring compounds were obtained selectively and diversely. In addition, the reaction raw materials are easily available, the operation is simple and safe, the conditions are mild, and the post-processing is simp...
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