316813-68-0

Upstream product

• 591-50-4 iodobenzene 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 108-86-1 bromobenzene 
• 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 
• 1006-64-0 (S)-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 

Relevant academic research and scientific papers

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.

SPIRO-1,1'-BIINDANE-7,7-BISPHOSPHINE OXIDES AS HIGHLY ACTIVE SUPPORTING LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC HECK REACTION

The present invention relates to catalyst complexes comprising palladium (Pd) and at least one spiro-1,1 '-biindane-7,7'- bisphosphine oxide ligand as disclosed herein, and their use. The present invention is further directed to the asymmetric Pd-catalyzed covalent carbon-carbon single bond formation from aryl, heteroaryl and alkenyl triflates and halides and olefins utilising the said catalyst complexes.

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.

Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline

The ring-closing metathesis (RCM) of two types of unsaturated chiral allylamines III, easily available from enantiomerically enriched epoxy alcohols, has been studied. Fully protected allylamines IIIa [1R = CH2-(CH2)n-CH=CH2; 2R = Boc; 3R = PMB] have been prepared from unsaturated epoxy alcohols, whereas bis-allylamines IIIb (1R = Ph, 2R = allyl, 3R = Boc or PMB) have been prepared from 2,3-epoxy-3-phenylpropanol. Both types have been subjected to RCM to provide either cyclic allylamine I or II. The synthetic potential of these intermediates has been demonstrated by the enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline.

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.