Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 32305-98-9, is researched, Molecular C31H32O2P2, about Copper-catalyzed enantioselective aminoboration of styrenes with 1,2-benzisoxazole as nitrogen source, the main research direction is copper catalyst enantioselective aminoboration styrene benzisoxazole.COA of Formula: C31H32O2P2.
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 β-aminoboronate which is a class of useful chiral compounds In this work, employing styrenes as substrates, 1,2-benzisoxazole as an electrophilic primary amine source, bis(pinacolato)diboron (B2pin2) 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 β-aminoalkylboranes, which could be readily converted to a class of valuable β-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 THF were added into a flame-dried tube. The resulting mixture was stirred at room temperature for 30 min. Then bis(pinacolato)diboron (B2pin2) (0.75 mmol), LiOCH3 (1.25 mmol), styrene 1 (0.5 mmol), 1,2-benzisoxazole (0.75 mmol) and another 2 mL of THF were added into the reaction system in sequence. The reaction tube was removed out from the glove box and stirred at 20°C for 12 h. After the reaction was finished, the NMR yield was firstly determined with di-Me 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 β-aminoboronates in moderate to good yields (47%∼84%) and enantioselectivities (81%∼99%). To demonstrate the utility of this reaction, β-boronate primary amine could be easily obtained by removing the Schiff base group of β-aminoboronate 3 under the methanol solution of hydroxylamine hydrochloride, which could be further oxidized to give corresponding chiral β-amino alc. in moderate yield (48%).
Different reactions of this compound((((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine))COA of Formula: C31H32O2P2 require different conditions, so the reaction conditions are very important.
Reference:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics