155155-73-0

Usage

Uses

Used in Pharmaceutical Development:
(2R,5R)-2,5-DIPHENYLPYRROLIDINE is used as a chemical intermediate for the development of pharmaceuticals due to its potential physicochemical and biological properties. Its unique structure and functional groups make it a valuable component in the synthesis of various drug molecules.
Used in Organic Synthesis:
(2R,5R)-2,5-DIPHENYLPYRROLIDINE is used as a building block in organic synthesis, allowing chemists to create a wide range of compounds with diverse applications. Its versatile structure and reactivity make it suitable for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
(2R,5R)-2,5-DIPHENYLPYRROLIDINE is utilized in chemical research to study its properties and explore its potential applications. Researchers investigate its reactivity, stability, and interactions with other molecules to gain insights into its behavior and possible uses in various chemical processes.

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-/m1/s1

Upstream product

• 56523-47-8 (R)-2-phenylpyrrolidine 
• 591-51-5 phenyllithium 
• 154777-23-8 (2R,5R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,5-bisphenylpyrrolidine 
• 536-74-3 phenylacetylene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 1083-56-3 1,4-diphenylbutane 
• 163580-98-1 (1S,4S)-1,4-diphenyl-1,4-butanediol bis(methanesulfonic acid ester) 
• 163580-95-8 (1S,4S)-1,4-diphenylbutane-1,4-diol 
• 214280-56-5 (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol 
• 495-71-6 phenacylacetophenone 
• 295328-86-8 (2S,5S)-N-allyl-2,5-diphenylpyrrolidine 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 192460-77-8 4-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-butene-2-one 

Relevant academic research and scientific papers

(R,R)-2,5-Diphenylpyrrolidine: Diastereoselective radical addition to the derived methacrylamide

Radical addition of thiophenol to the methacrylamide 1 proceeds with high diastereoselectivity, to give 2 and 3 in a ratio of 25:1.

Asymmetric Synthesis of Enantiopure Pyrrolidines by C(sp3)?H Amination of Hydrocarbons

The asymmetric synthesis of enantiopure pyrrolidines is reported via a streamlined strategy relying on two sequential C?H functionalizations of simple hydrocarbons. The first step is a regio- and stereoselective catalytic nitrene C?H insertion. Then, a su

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

Direct α-C-H bond functionalization of unprotected cyclic amines

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.

A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis

A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).

Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B

Iodocyclization of sulfinimine-derived enantiopure homoallylic sulfonamides affords trans-2,5-disubstituted 3-iodopyrrolidines and represents valuable methodology for the asymmetric synthesis of this important heterocyclic ring system.

Asymmetric synthesis of trans-2,5-diphenylpyrrolidine: A C2-symmetric chiral amine

(R,R)-2,5-Diphenylpyrrolidine of high enantiomeric purity (>98% e.e.) may be prepared from 1,4-diphenyl-1,4-butanedione in 4 steps and 64% overall yield. A key step is asymmetric reduction of the dione with Ipc2BCl.

Diastereoselective addition of chiral imines and 1,3-oxazolidines with Grignard reagents; asymmetric synthesis of (R)-2-aryl- and (R,R)-2,5-bis(aryl)pyrrolidines

Asymmetric syntheses of (R)-2-aryl- and (R,R)-2,5-bis(aryl)pyrrolidines were described starting from chiral aromatic imines derived from (R)-phenylglycinol, in which the diastereoselective additions of Grignard reagents to the chiral imines and 1,3-oxazol