Research speed reading in 2021. Chemistry, like all the natural sciences, begins with the direct observation of nature— in this case, of matter. Recommanded Product: Octanedioic acid, The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction. 505-48-6, Name is Octanedioic acid, molecular formula is C8H14O4. In an article, author is Huang Hao,once mentioned of 505-48-6.
Organoboron compounds are important intermediates in organic synthesis because of their high utilities for C-C and C-X bond formations. Transition metal-catalyzed borylative difunctionalization of alkenes, which can simultaneously introduce C-B, C-C or C-X bonds, could directly construct highly functionalized organoboron in one step. Among these reactions, copper catalyzed enantioselective aminoboration of styrenes is an efficient approach to generate enantioriched beta-aminoboronate which is a class of useful chiral compounds. In this work, employing styrenes as substrates, 1,2-berrzisoxazole as an electrophilic primary amine source, bis(pinacolato)diboron (B(2)pin(2)) as boron source and LiOCH3 as base, an enantioselective Cu-catalyzed aminoboration of styrenes by using a chiral sulfoxide-phosphine (SOP) ligand was developed, and a board range of chiral beta-aminoalkylboranes, which could be readily converted to a class of valuable beta-hydroxylalkylamines, were accessed with high yields and ee values. A general procedure for this aminoboration of styrenes is described in the following: in a glove box, CuI (0.05 mmol), chiral sulfoxide phosphine ligand L1 (0.06 mmol), and 2 mL of anhydrous tetrahvdrofuran were added into a flame-dried tube. The resulting mixture was stirred at room temperature for 30 min. then bis(pinacolato)diboron (B(2)pin(2)) (0.75 mmol), LiOCH3 (1.25 mmol), styrene 1 (0.5 nunol), 1,2-benzisoxazole (0.75 mmol) and another 2 mL of THE were added into the reaction system in sequence. The reaction tube was removed out from the glove box and stirred at 20 degrees C for 12 h. After the reaction was finished, the NMR yield was firstly determined with dimethyl terephthalate (9.7 mg, 0.05 mmol) as internal standard, then, the crude product was recovered and purified with a preparative TLC which was alkalized with triethylamine to give the desired beta-aminoboronates in moderate to good yields (47%similar to 84%) and enantioselectivities (81%similar to 99%). To demonstrate the utility of this reaction, beta-boronate primary amine could be easily obtained by removing the Schiff base group of beta-aminoboronate 3 under the methanol solution of hydroxylamine hydrochloride, which could be further oxidized to give corresponding chiral beta-amino alcohol in moderate yield (48%).
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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics