295328-85-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(2S,5S)-2,5-Diphenylpyrrolidine serves as a fundamental building block in the synthesis of a range of pharmaceuticals and agrochemicals. Its role in these industries is pivotal for creating new molecules with therapeutic or pesticidal properties, leveraging its structural and chiral attributes to influence the activity and selectivity of the resulting compounds.
Used as a Ligand in Asymmetric Catalysis:
In the realm of catalysis, (2S,5S)-2,5-diphenylpyrrolidine is employed as a ligand, facilitating asymmetric reactions that produce enantiomerically pure products. Its chiral nature is instrumental in controlling the stereochemistry of the reactions, leading to the preferential formation of one enantiomer over another, which is essential in the production of biologically active compounds.
Used in Organic Synthesis as Chiral Auxiliaries:
(2S,5S)-2,5-Diphenylpyrrolidine is utilized as a chiral auxiliary in organic synthesis, providing a source of asymmetry to guide the stereoselective formation of complex molecules. Its rigid structure and defined stereochemistry make it a valuable tool for achieving high levels of enantioselectivity in various synthetic transformations.
Used in the Study of Molecular Conformations and Stereochemistry:
The rigid structure of (2S,5S)-2,5-diphenylpyrrolidine makes it a useful probe in the study of molecular conformations and stereochemistry. Researchers can use (2S,5S)-2,5-DIPHENYLPYRROLIDINE to investigate the spatial arrangements of molecules and understand the implications of stereochemistry on molecular interactions and reactivity.

InChI:InChI=1/C16H17N/c1-3-7-13(8-4-1)15-11-12-16(17-15)14-9-5-2-6-10-14/h1-10,15-17H,11-12H2/t15-,16-/m0/s1

Upstream product

• 295328-86-8 (2S,5S)-N-allyl-2,5-diphenylpyrrolidine 
• 495-71-6 phenacylacetophenone 
• 214280-56-5 (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol 
• 295328-90-4 (1R,4R)-1,4-bis(methanesulfonyloxy)-1,4-diphenylbutane 
• 70-11-1 α-bromoacetophenone 
• 1376191-10-4 C₃₃H₃₉N 
• 1376191-15-9 C₁₆H₁₅N 
• 1569095-70-0 (2E)-N-methoxy-N-((1S)-1-phenylprop-2-en-1-yl)but-2-enamide 
• 1569095-79-9 (5S)-1-methoxy-5-phenylpyrrolidin-2-one 
• 100-58-3 phenylmagnesium bromide 
• 1569095-73-3 C₁₁H₁₁NO₂ 

Downstream Products

• 919087-08-4 (E)-1-((2S,5S)-2,5-Diphenyl-pyrrolidin-1-yl)-3-phenyl-propenone 
• 1072809-78-9 (S,Z)-N,N-[(1S,4S)-1,4-diphenyl-1,4-butylidene]-5-phenyl-3-hexenamide 
• 1072809-60-9 (R,Z)-N,N-[(1S,4S)-1,4-diphenyl-1,4-butylidene]-5-phenyl-3-hexenamide 
• 1072809-81-4 (2R)-N,N-[(1'S,4'S)-1',4'-diphenyl-1',4'-butylidene]-2-[(benzyloxy)methyl]octanamide 
• 1376191-10-4 C₃₃H₃₉N 
• 35657-63-7 trans-N-Methyl-2,5-diphenylpyrrolidin 
• 444667-33-8 (2S,5S,11aR)-1-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2,5-diphenylpyrrolidine 
• 875275-34-6 ((4R,5R)-3,4-Diphenyl-4,5-dihydro-isoxazol-5-yl)-((2S,5S)-2,5-diphenyl-pyrrolidin-1-yl)-methanone 
• 1355611-19-6 C₂₆H₂₆N₂O₃ 
• 1355611-47-0 C₃₀H₃₂N₂O₂S 
• 1355611-46-9 C₃₂H₃₄N₂O₄S 

Relevant academic research and scientific papers

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides

In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of

Addition of organometallic reagents to chiral N-methoxylactams: Enantioselective syntheses of pyrrolidines and piperidines

Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compou

Mukaiyama-Michael reactions with acrolein and methacrolein: A catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins

Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

Efficient preparation of optically pure C2-symmetrical cyclic amines for chiral auxiliary

Optically pure C2-symmetrical amines were efficiently synthesized from the corresponding diols obtained from the enantioselective borohydride reduction of the diketones catalyzed by the optically active β-ketoiminato cobalt(II) complex.

A simple enantioselective preparation of (2S,5S)-2,5-diphenylpyrrolidine and related diaryl amines

A short efficient catalytic asymmetric route to the preparation of C2-symmetric diaryl cyclic amines is described. Copyright (C) 2000 Elsevier Science Ltd.