316813-68-0

Basic information

• Product Name: (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole
• Synonyms: (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole
• CAS NO: 316813-68-0
• Molecular Weight: 245.321
• Mol File: 316813-68-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole(316813-68-0)
• EPA Substance Registry System: (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole(316813-68-0)

Safety Data

• Hazardous Substances Data: 316813-68-0(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 591-50-4 iodobenzene 
• 316813-33-9 Allyl-((E)-(R)-2-benzenesulfonyl-1-phenyl-but-2-enyl)-amine 
• 316813-29-3 (E)-(R)-2-Benzenesulfonyl-1-phenyl-but-2-enylamine 
• 316813-12-4 (1R,2S)-2-Benzenesulfonyl-1-phenyl-but-3-enylamine 
• 316813-41-9 Allyl-((Z)-(S)-1-phenyl-but-2-enyl)-amine 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 13139-12-3 tert-butyl 2,5-dioxopyrrolidin-1-yl carbonate 
• 474558-78-6 Allyl-((1R,2R)-2,3-dihydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 474558-77-5 (2R,3R)-3-allylamino-3-phenylpropane-1,2-diol 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 474558-80-0 (1S)-N-allyl-N-(tert-butoxycarbonyl)-1-phenylallylamine 

Downstream Products

• 474558-82-2 (2R,3R,4S)-N-tert-butoxycarbonyl-3,4-dihydroxy-2-phenylpyrrolidine 
• 474558-83-3 (2R,3R,4S)-(-)-N-tert-butoxycarbonyl-3,4-dihydroxy-2-phenyl-pyrrolidine isopropylidene acetal 
• 174310-75-9 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1006-64-0 (S)-2-phenylpyrrolidine 

Relevant articles and documents

Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions

A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.

Asymmetric intermolecular heck reaction of aryl halides

The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates. Herein, we extend the reaction to aryl and vinyl bromides. Various cyclic olefins coupled with high enantioselectivity. Only bisphosphine oxides on a spiro backbone formed highly stereoselective Pd catalysts. The use of alcoholic solvents and alkylammonium salts were essential to promote halide dissociation from neutral arylpalladium complexes.

Synthesis of enantiopure pyrrolidine and piperidine derivatives via ring closing metathesis

The additions of lithiated allylsulfone carbanion to chiral N-sulfinylimines were found to proceed with good to excellent selectivity. The resulting intermediates 4a-d after transformation to dienylamides 7a-d and 16a-d, were converted to functionalized enantiopure piperidines and pyrrolines, respectively, via ring closing metathesis (RCM). (C) 2000 Elsevier Science Ltd.