7547-97-9

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant for the preparation of alkynylphenoxyacetic acids, which act as DP2 receptor antagonists. These antagonists are crucial for the treatment of allergic inflammatory diseases, providing relief from symptoms and managing the underlying inflammation.
Used in Organic Synthesis:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in palladium-phosphine-catalyzed Suzuki-Miyaura coupling reactions. This reaction is a powerful tool in organic synthesis, allowing for the formation of carbon-carbon bonds between an organoboron compound and an organohalide, leading to the creation of a wide range of complex organic molecules.
Used in Biochemical Research:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant for the preparation of tetrahydrobenzothiophenes. These compounds serve as conformationally restricted enol-mimic inhibitors of type II dehydroquinase. This makes them valuable in biochemical research, particularly in the study of enzyme mechanisms and the development of potential therapeutic agents.
Used in Organic Chemistry:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in Cu(II)-mediated Ullmann-type coupling. This reaction is an important method for forming carbon-carbon bonds, particularly in the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and materials science.
Used in Advanced Synthesis Techniques:
TRANS-1-PROPEN-1-YLBORONIC ACID is used in the preparation of highly substituted benzannulated cyclooctanol derivatives. This is achieved through samarium diiodide-mediated cyclization, a technique that allows for the formation of complex ring systems with multiple stereocenters, which are often found in biologically active natural products and pharmaceuticals.
Used in Stereoselective Synthesis:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in nickel-catalyzed three-component reductive coupling with alkynes and enones. This reaction provides a route to stereospecific dienes, which are important building blocks in the synthesis of natural products and pharmaceuticals, as well as materials with unique properties.

InChI:InChI=1/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2+

Upstream product

• 121-43-7 Trimethyl borate 
• 13154-14-8 1-propenylmagnesium bromide 
• 14560-05-5 (1-propenyl)dichlorobrane 
• 1104637-46-8 C₈H₁₂BNO₄ 
• 74-99-7 prop-1-yne 
• 55671-55-1 dibromoborane dimethylsulfide 
• 1310-73-2 sodium hydroxide 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 590-13-6 (Z)-1-propenyl bromide 
• 5419-55-6 Triisopropyl borate 
• 6524-17-0 (Z)-1-propenyllithium 
• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 75-07-0 acetaldehyde 
• 1594-94-1 allyl dimethyl boronic acid ester 

Downstream Products

• 83947-59-5 (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane 
• 83947-58-4 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane 
• 104-46-1 anethole 
• 14918-24-2 β-methyl-3-methylstyrene 
• 14918-25-3 1,3-dimethyl-2-(prop-1-en-1-yl)benzene 
• 324529-86-4 (E/Z)-2-(prop-1-enyl)benzaldehyde 
• 73930-99-1 1-nitro-2-(prop-1-en-1-yl)benzene 
• 637-50-3 1-phenylpropene 
• 943341-56-8 C₂₀H₁₉BrO₄ 
• 1315277-99-6 C₂₄H₃₀O₄ 
• 1312794-28-7 C₁₆H₁₆O₃ 
• 1399813-88-7 4-[(Z)-3-(prop-1-enyl)benzyl]benzaldehyde 
• 1399813-86-5 (Z)-1-[4-(4-fluorobenzyl)phenyl]prop-1-ene 
• 1429614-79-8 C₂₅H₁₉N₃NiO₃ 

Relevant academic research and scientific papers

A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates

Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution

The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed

Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.

Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process

A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allylboronic acid together with (S)-α-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic α-amino acid derivatives.

Enantioselective syn and anti homocrotylation of aldehydes: Application to the formal synthesis of spongidepsin

Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereoselectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.

Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives

A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments. Polyols: The reported copper-catalyzed oxy-alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn-1,3-carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.

Construction of multiple, contiguous quaternary stereocenters in acyclic molecules by lithiation-borylation

Lithiation of carbamates followed by borylation provides a powerful method for the homologation of boron reagents. However, when applied to hindered systems (secondary carbamates with tBu-boronic esters) for the construction of two quaternary centers, thi

SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS

Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.

Enantioselective homocrotylboration of aliphatic aldehydes

A practical route to optically pure syn-homocrotylation reagents is described, including highly diastereo- and enantioselective preparation of numerous syn-homocrotyl products, as well as several matched mismatched pairs. NMR experiments suggest that the active homocrotylating species is a cyclopropylcarbinyldichloroborane generated by chloride exchange from the PhBCl2 activator. Computational studies support the intermediacy of chloroboranes and suggest that homoallyl/homocrotyl transfers occur through Zimmerman-Traxler transition states.