249617-46-7

Usage

Uses

Used in Pharmaceutical Industry:
(5S)-5-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]diphenylMethyl]-2-Pyrrolidinone is used as a building block for the synthesis of various drugs. Its unique structure and functional groups contribute to the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, (5S)-5-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]diphenylMethyl]-2-Pyrrolidinone serves as a reagent, facilitating the formation of new chemical bonds and the synthesis of complex organic molecules.
Used as a Protective Group:
(5S)-5-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]diphenylMethyl]-2-Pyrrolidinone is also utilized as a protective group for hydroxyl and amino groups in organic chemistry. Its ability to shield these functional groups during chemical reactions allows for greater control over the reaction outcomes and the synthesis of desired products.
Used in Agrochemicals:
(5S)-5-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]diphenylMethyl]-2-Pyrrolidinone has potential applications in the agrochemical industry, where it may be used to develop new compounds for pest control, crop protection, or other agricultural purposes.
Used in Materials Science:
(5S)-5-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]diphenylMethyl]-2-Pyrrolidinone's structural properties and functional groups also make it a candidate for applications in materials science, where it could be used to create new materials with specific properties or to improve existing materials for various applications.

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 149561-81-9 (-)-(S)-5-(Hydroxydiphenylmethyl)pyrrolidin-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 4931-66-2 methyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 108-86-1 bromobenzene 

Downstream Products

• 1005210-14-9 (S)-5-{[(tert-butyldimethylsilyl)oxy]diphenylmethyl}-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 
• 1414773-52-6 (S)-5-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium chloride 
• 1447813-89-9 (S)-5-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)-2-(2,6-dimethoxyphenyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]riazol-2-ium chloride 
• 1447823-15-5 (S,Z)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)-5-(2-(2,6-dimethoxyphenyl)hydrazono)pyrrolidine hydrochloride 
• 1447813-88-8 (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)-5-methoxy-3,4-dihydro-2H-pyrrole 
• 260391-10-4 tert-butyl (3-{(2S)-[(tert-butyldimethylsilyloxy)diphenylmethyl]-5-thioxopyrrolidin-1-yl}propyl)carbamate 
• 260391-09-1 tert-butyl (3-{(2S)-[(tert-butyldimethylsilyloxy)diphenylmethyl]-5-oxopyrrolidin-1-yl}propyl)carbamate 
• 260391-08-0 1-(3-amino-propyl)-5-[(tert-butyl-dimethyl-silanyloxy)-diphenyl-methyl]-pyrrolidin-2-one 
• 260391-11-5 tert-butyl (3-[(2S)-(hydroxydiphenylmethyl)-5-thioxopyrrolidin-1-yl]propyl)carbamate 
• 260391-07-9 3-{(2S)-[(tert-butyldimethylsilyloxy)diphenylmethyl]-5-oxopyrrolidin-1-yl}propionitrile 

Relevant academic research and scientific papers

N-Heterocyclic carbene triazolium salts containing brominated aromatic motifs: Features and synthetic protocol

In this work, we provide a brief overview of the role of N-aryl substituents on triazolium N-heterocyclic carbene (NHC) catalysis. This synopsis provides context for the disclosed synthetic protocol for new chiral N-heterocyclic carbene (NHC) triazolium salts with brominated aromatic motifs. Incorporating brominated aryl rings into NHC structures is challenging, probably due to the substantial steric and electronic influence these substituents exert throughout the synthetic protocol. However, these exact characteristics make it an interesting N-aryl substituent, because the electronic and steric diversity it offers could find broad use in organometallic- A nd organo-catalysis. Following the synthetic reaction by NMR guided the extensive modification of a known protocol to enable the preparation of these challenging NHC pre-catalysts.

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral

Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94% ee) or α-chloroesters (up to 94% ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.

Highly enantioselective intermolecular stetter reaction of simple acrylates: Synthesis of α-chiral γ-Ketoesters

Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding versatile α-chiral γ-ketoesters. This represents the first catalytic asymmetric route towards these valuable compounds (see scheme).

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Chiral N-heterocyclic carbene catalyzed staudinger reaction of ketenes with imines: Highly enantioselective synthesis of N-boc β-lactams

(Chemical Equation Presented) N-Heterocyclic carbenes (NHCs) were demonstrated to be efficient catalysts for the Staudinger reaction of ketenes with N-tosyl, N-benzyloxycarbonyl, or N-tert-butoxycarbonyl imines. Chiral NHC 8b, conveniently prepared from L

Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation

A family of enantiopure 1,2,4-triazolium salts were prepared starting from the inexpensive (S)-pyroglutamic acid. After treatment with base, the corresponding N-heterocyclic carbenes were tested as organocatalysts in the asymmetric benzoin condensation and gave good yields and up to 95% ee.

Asymmetric dimerization of disubstituted ketenes catalyzed by N-heterocyclic carbenes

A series of chiral N-heterocyclic carbenes (NHCs), derived from L-pyrogutamic acid, were found to be efficient catalysts for the asymmetric dimerization of alkylarylketenes to give the corresponding α-quaternary β-alkylidenyl-β-lactones in good yields with up to 97% ee. A chiral NHC with a proximal hydroxy group is superior in comparison with the corresponding NHC with its hydroxy group protected.

(S)-Pyroglutamic acid, (S)-malic acid, and (S)-serine as useful starting materials in the synthesis of enantiopure hydroxyamidines

The synthesis of four enantiopure hydroxyamidines is described. One amidine was obtained from (S)-pyroglutamic acid. Its key step involved the addition of phenylmagnesium bromide to the corresponding ester, affording the tertiary alcohol without detectabl

Asymmetric protonation of lithium enolate using 5-substituted pyrrolidin-2-one as a chiral proton source

Asymmetric protonation of the lithium enolate moiety of a 2-substituted α-tetralone (3,4-dihydronaphthalen-1(2H)-one) was examined using 5-substituted pyrrolidin-2-ones as chiral proton sources. Among the three types of pyrrolidin-2-ones bearing either a