81532-35-6

Upstream product

• 81532-40-3 N-Benzyl-N-(9H-fluoren-9-yl)-4-methyl-benzenesulfonamide 
• 525-03-1 9-aminofluorene 
• 100-52-7 benzaldehyde 
• 2157-52-0 9-fluorenone oxime 
• 100-46-9 benzylamine 
• 81532-38-9 9-(N-Benzylamino)fluorene 
• 6630-65-5 9-chlorofluorene 

Downstream Products

• 1072879-68-5 (2R,3R)-cis-1-N-9-fluorenyl-2-carboxyethyl-3-phenylaziridine 
• 283157-03-9 2-(9H-fluoren-9-ylamino)-2-phenylacetonitrile 

Relevant academic research and scientific papers

End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives

The invention belongs to the field of chemical medicines, and particularly relates to end-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives. In the method, the end-substituted homoallylic amine derivatives are prepared by allowing a 2-aza-allyl anion to participate, in a high regioselectivity manner, an allylation reaction catalyzed by iridium, and by an intramolecular 2-aza-Cope rearrangement reaction. The derivatives can be synthesized efficiently by the method. The method is simple, convenient and feasible. Prepared compounds have extremely high optical purity. The derivatives prepared by the method can be used for preparing Sertraline and Tametraline which are anti-depression medicines and some natural products.

Catalytic Asymmetric Umpolung Allylation of Imines

Here we report an iridium-catalyzed asymmetric umpolung allylation of imines as a general approach to prepare 1,4-disubstituted homoallylic amines, a fundamental class of compounds that are hitherto not straightforward to obtain. This transformation proceeds by a cascade involving an intermolecular regioselective allylation of 2-azaallyl anions and a following 2-aza-Cope rearrangement, utilizes easily available reagents and catalysts, tolerates a substantial scope of substrates, and readily leads to various enantioenriched, 1,4-disubstituted homoallylic primary amines.

Catalytic imine-imine cross-coupling reactions

We report here efficient catalytic imine-imine cross-coupling reactions based on an umpolung strategy; an imine bearing a 9-fluorenyl moiety on its nitrogen atom, which acted as a nucleophile, reacted with another imine to afford an imine-imine cross-coupling adduct in high yield. Furthermore, a chiral guanidine acted as a chiral catalyst for these coupling reactions, and optically active 1,2-diamines were obtained in high yields with high enantioselectivities. This journal is

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

Chiral lanthanum(III)-binaphthyldisulfonate complexes for catalytic enantioselective strecker reaction

A catalytic enantioselective Strecker reaction catalyzed by novel chiral lanthanum(III)-binaphthyl disulfonate complexes was developed. The key to promoting the reactions was a semistoichiometric amount of AcOH or i-PrCO2H, which takes advantage of HCN ge

A catalytic asymmetric Strecker-type reaction promoted by Lewis acid-Lewis base bifunctional catalyst

A general asymmetric Strecker-type reaction is reported, catalyzed by the Lewis acid-Lewis base bifunctional catalyst 1. The reaction of trimethylsilyl cyanide (TMSCN) with various fluorenyl imines, including n-aldimines and α,β-unsaturated imines, proceeds with good to excellent enantioselectivities in the presence of a catalytic amount of phenol as additive (20 mol%) (catalytic system 1). The products were successfully converted to the corresponding amino acid derivatives in high yields without loss of enantiomeric purity. Furthermore, hydrogenation or dihydroxylation of the products from α,β-unsaturated imines afforded saturated or functionalized aminonitriles also without loss of enantiomeric purity. The absolute configuration of the products and a control experiment using catalyst 2 supported the proposed dual activation of the imine and TMSCN by the Lewis acid (Al) and the Lewis base moiety (phosphine oxide) of 1. From the mechanistic studies including kinetic and NMR experiments of the catalytic species, the role of PhOH seems to be a proton source to protonate the anionic nitrogen of the intermediate. Specifically, we have found that TMSCN is more reactive than HCN in this catalytic system, probably due to the activation ability of the phosphine oxide moiety of 1 toward TMSCN. This fact prompted us to develop the novel catalytic system 2, consisting of 1 (9 mol%), TMSCN (20 mol%) and HCN (1.2 mol eq). This new system afforded comparable results with obtained by system 1 (1 (9 mol%)-TMSCN (2 mol eq)-PhOH (20 mol%)).

Activated C,H-Acids: N-Alkyl-9-fluorenimines

N-Substituted 9-fluoremines 1 are easily prepared from primary amines or aminoesters and 9-fluorenimine: their conjugate carbanions 2 are formed by the action of alkoxides and are reprotonated to 1 or to the tautomeric 9-alkylidenaminofluorenes 3 dependin