59159-39-6

Usage

Uses

Used in Pharmaceutical Industry:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for the rhodium-catalyzed asymmetric hydrogenation reactions, which are crucial for the synthesis of chiral compounds with potential pharmaceutical applications. The enantioselective reduction of prochiral substrates can lead to the production of biologically active molecules with desired stereochemistry.
Used in Organic Chemistry Research:
In the field of organic chemistry, (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for the Wittig reaction, a widely employed method for the synthesis of alkenes from aldehydes and ketones. This reaction allows for the formation of carbon-carbon double bonds, which are essential structural elements in many organic compounds.
Used in Synthesis of Complex Molecules:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for Wittig methylenation, a specific type of Wittig reaction that involves the conversion of aldehydes and ketones into methylene compounds. This process is useful for the synthesis of complex organic molecules with specific structural requirements.
Used in the Preparation of Chiral Ligands:
This phosphonium salt is used in the preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via a double aza-Michael addition reaction. The resulting chiral ligands can be employed in asymmetric catalysis, enabling the selective formation of enantiomerically pure compounds.
Used in Fluorination Reactions:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used for the stereoselective preparation of α-fluoro-α,β-unsaturated esters. This involves deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes, allowing for the synthesis of fluorinated compounds with specific stereochemistry.
Used in Chain Extension Reactions:
In organic synthesis, (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used for Wittig chain extension reactions, which involve the elongation of carbon chains in organic molecules. This process is valuable for the synthesis of long-chain compounds and polymers with tailored properties.

InChI:InChI=1/C24H26O2P/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18H,19H2,1-3H3/q+1

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 603-35-0 triphenylphosphine 

Downstream Products

• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 106893-76-9 4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester 
• 131619-26-6 tert-butyl (Z)-5-phenyl-2-pentenoate 
• 131619-25-5 5-phenyl-2(E)-pentenoic acid tert-butyl ester 
• 845883-04-7 tert-butyl 3,4-dihydroxycinnamate 
• 201221-73-0 fluoro-(triphenyl-λ⁵-phosphanylidene)-acetic acid tert-butyl ester 
• 144374-53-8 4-[2-(tert-butoxycarbonyl)ethenyl]benzaldehyde 
• 180515-27-9 tert-Butyl 3-(E)-<2-<(E)-2-(tert-butoxycarbonyl)ethenyl>phenyl>acrylate 
• 170282-61-8 C₁₄H₁₆O₃ 
• 209344-13-8 4-nitrophenylacrylic acid tert-butyl ester 
• 942232-49-7 tert-butyl 3-nitrocinnamic acid 
• 103890-69-3 (E)-3-(2-formylphenyl)-2-propenoic acid 1,1-dimethylethylester 
• 1218938-27-2 (E)-3-(3-fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester 
• 103890-78-4 Lacidipine 

Relevant academic research and scientific papers

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones

An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates

A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Side-Chain Modification of Peptides Using a Phosphoranylidene Amino Acid

The flexible variation of peptidomimetics is of great interest for the identification of optimized protein ligands. Here we present a general concept for introducing side-chain modifications into peptides using triarylphosphonium amino acids. Building blo

Asymmetric Catalytic Diverse Ring Opening/Cycloadditions of Cyclobutenones with (E)-Alkenyloxindoles and (E)-Dioxopyrrolidines

Highly enantioselective ring-opening/cycloaddition reactions of cyclobutenones were achieved by employing chiral N,N′-dioxide/metal complexes as the catalysts. The Diels-Alder type cycloaddition with (E)-alkenyloxindoles yielded spirocyclohexaneoxindoles with excellent results. Meanwhile, a hetero-Diels-Alder process occurred with (E)-dioxopyrrolidines to afford spiropyrrolidinone-dihydropyranone derivatives.

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.

A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides

A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).

Methyl caffeate as an α-glucosidase inhibitor from solanum torvum fruits and the activity of related compounds

In screening experiments for rat intestinal α-glucosidase (sucrase and maltase) inhibitors in 325 plants cultivated in Japan's southern island, of Tanegashima, marked inhibition against both sucrase and maltase was found in the extract of the fruit of Solanum torvum. Enzyme-assay guided fractionation of the extract led to the isolation of methyl caffeate (1) as a rat intestinal sucrase and maltase inhibitor. We examined 13 caffeoyl derivatives for sucrase- and maltase-inhibitory activities. The results showed that methyl caffeate (1) had a most favorable structure for both sucrase and maltase inhibition, except for a higher activity of methyl 3,4,5-trihydroxycinnamate (14) against sucrase. Its moderate inhibitory action against α-glucosidase provides a prospect for antidiabetic usage of S. torvum fruit.