A kind of synthetic method of novel chiral nitrobinaphthol and its derivatives
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A technology of nitrobinaphthol and synthesis method, which is applied in the field of organic synthesis, can solve the problems of many by-products, pollute the environment, and low atom economy, and achieve the effect of less reaction by-products and mild conditions
Active Publication Date: 2020-11-27
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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This method has mature technology and low cost, but low atom economy, serious environmental pollution and many by-products
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Embodiment 1
[0028] Embodiment 1: the target product in the present embodiment is:
[0029] Specifically, it is realized by the following steps:
[0030] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 5mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 92%.
Embodiment 2
[0031] Embodiment 2: the target product in the present embodiment is:
[0032] Specifically, it is realized by the following steps:
[0033] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 5mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed by using an instrument, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 95%.
Embodiment 3
[0034] Embodiment 3: the target product in the present embodiment is:
[0035] Specifically, it is realized by the following steps:
[0036] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 2mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 93%.
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Abstract
The invention relates to a synthesizing method of novel chiral nitro binaphthol and derivatives thereof, and belongs to the field of organic synthesis. A novel green free radical nitrifying method isprovided, and comprises the following steps of using chiral binaphthol as the raw material, and generating free radical nitrifying reaction with a green nitrifying reagent (TBN (tert-butyl nitrite)) at room temperature by using tetrahydrofuran as a reaction solvent, so as to obtain the chiral nitro binaphthol. The synthesizing method has the advantages that the metal is not used in reaction, and the TBN is directly used in the nitrifying reaction; only the product and tertiary butanol are generated in reaction, and the pollution to environment is reduced; the important application prospect isrealized in the synthesizing field of the chiral nitro binaphthol, the green nitrifying is truly realized, and a novel concept is provided for the large-scale industrialized production of the nitro binaphthol.
Description
technical field [0001] The invention relates to a method for preparing novel chiral nitrobinaphthol and derivatives thereof, in particular to a method for preparing chiral phosphoric acid and chiral phosphorus ligands, and belongs to the field of organic synthesis. Background technique [0002] In 1873, Von Richter first reported the synthesis of the racemate of binaphthol (BINOL) (structural formula 1). However, it was not until the 1970s that chiral BINOL was prepared and its absolute configuration determined. The two naphthalene rings in the binaphthol structure are bulky, so the steric hindrance is large and rigid, and because of the coaxial effect between the two rings, there is still room for rotation and flexibility. Chiral binaphthol and its derivatives have strong chiral induction, and have been widely used in asymmetric alkylation of aldehydes, asymmetric reduction of ketones, asymmetric Mannich reactions, asymmetric MBH reactions, asymmetric Many important organ...
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