15148-17-1

Upstream product

• 13474-22-1 1,4-diphenyl-azetidin-2-one 
• 3556-76-1 ethyl (2Z)-3-phenyl-3-(phenylamino)prop-2-enoate 
• 538-51-2 benzylidene phenylamine 
• 10387-40-3 potassium thioacetate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 62-53-3 aniline 
• 6049-56-5 N-Phenyl-β-phenyl-β-alanine 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 100-52-7 benzaldehyde 
• 109-99-9 tetrahydrofuran 

Relevant academic research and scientific papers

Parallel synthesis using Mannich-type three-component reactions and 'field synthesis' for the construction of an amino alcohol library

An amino alcohol library was constructed by parallel synthesis based on Mannich-type three-component reactions of aldehydes, amines, and polymer-supported silyl enol ethers, followed by reductive cleavage from the supports. 'Field Synthesis', which provid

5(4'-Chloromethylphenyl)pentylpolystyrene resin (CMPP resin). A new linker resin for solid-phase organic synthesis under Lewis acidic conditions

A new linker resin for solid-phase organic synthesis under Lewis acidic conditions has been developed. The resin, 5-(4'-chloromethylphenyl)pentylpolystyrene resin (CMPP resin), has no oxygen or nitrogen atoms in its spacer moiety. Imino aldol reactions of polymer-supported silyl enol ethers using the new resin with imines were demonstrated in the presence of a Lewis acid, and it was shown that the yields using CMPP resin were much higher (ca. 10-30%) than those using Merrifield resin.

Gold-Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Catalytic Reaction Pathways to Access 1,3-Amino Alcohols, 3-Hydroxyketones, or 3-Aminoketones

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. First, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxyimines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-amino alcohols with high syn selectivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway. The utility of the new chemistry was exemplified by the one-pot synthesis of a selection of N-arylpyrrolidines and N-arylpiperidines. A mechanism for the hydroamination has been proposed on the basis of experimental studies and density functional theory calculations.

Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library

Polymer-supported silyl enol ethers (thioketene silyl acetals) were prepared from chloromethyl copoly-(styrene-1%-divinylbenzene) resin. The silyl enol ethers reacted with imines in the presence of a catalytic amount of scandium triflate (Sc(OTf)3) to afford β-amino thioesters, which were reduced to amino alcohols in good yields. These reactions provide a convenient method for the preparation of an amino alcohol library.

Chemo- and diastereoselective reduction of β-enamino esters: A convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters

Convenient procedures for the chemo- and diastereoselective reduction of b-enamino esters 1 are described. Both cis- and trans-γ-amino alcohols 2 or b-amino esters 3 can be prepared by reduction of b-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Na/i-PrOH or NaHB(OAc)3/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric γ-amino alcohols 2 and β-amino esters 3 obtained are established by 1H and 13C NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.

Reduction of N-Substituted Azetidin-2-ones to Azetidines

Reduction of N-substituted azetidin-2-ones to N-substituted azetidines was accomplished rapidly and in good yield with diborane in tetrahydrofuran and with alane in ether.The stereochemistry of the ring substituents was retained under the reaction conditi