99566-43-5

Upstream product

• 557-20-0 diethylzinc 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 75391-07-0 (E)-2-methyl-1-phenyl-1-pentene-3-one 
• 99603-85-7 (E)-(+/-)-1-ethynyl-2-methyl-3-phenyl-2-propenyl acetate 
• 99566-38-8 (E)-(R)-1-ethynyl-2-methyl-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Enantioselectivity switch controlled by N,N′-di- or N,N,N′,N′-tetra-substituted chiral thiophosphorodiamide ligands, structural relatives of thioureas, in catalytic additions of diethylzinc to aldehydes

We have developed a series of new chiral thiophosphorodiamide ligands derived from (1R,2R)-(+)-1,2-diphenylethylenediamine, which are the structural relatives of thioureas. An investigation into their catalytic properties in asymmetric additions of diethylzinc to aldehydes has shown that N,N,N′,N′-tetra-substituted chiral thiophosphorodiamides can give (R)-secondary alcohols with up to 98% yield and 98% ee, while N,N′-di-substituted chiral thiophosphorodiamides give (S)-secondary alcohols with up to 99% yield and 97% ee values. The enantioselectivity switch is highly efficient with a broad substrate scope. We have also proposed hypothetical reaction pathways, which result in an enantioselectivity switch.

Asymmetric preparation of new N, N -dialkyl-2-amino-1,1,2-triphenylethanol catalysts and a kinetic resolution in the addition of diethylzinc to flavene-3-carbaldehydes

Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N-substituents of the catalysts led us to identify N-methyl-N-(S)-1-phenyl-ethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3- carbaldehydes with the chiral catalyst.

Enantioselective one-pot catalytic synthesis of 4,5-epoxy-3-alkanols and 1-Phenyl-2,3-epoxy-1-alkanols from α,β-unsaturated aldehydes

Conformationally restricted perhydrobenzoxazines have been demonstrated to be good chiral ligands for one-pot asymmetric ethylation/epoxidation, and the unprecedented arylation/epoxidation of trisubstituted α,β-unsaturated aldehydes. The scope of the reaction has been studied and a wide set of substrates with allylic strain of different nature has been explored, obtaining good or total diastereoselectivities in all cases. The enantiocontrol was good or high for the ethylation/epoxidation reaction, whereas it remained at moderate or good levels for the arylation/epoxidation. The reaction is general for trisubstituted enals, and alkylic and aromatic substituents are tolerated at both the α- and β-position of the unsaturated aldehyde; however, disubstituted enals remain challenging substrates. When the one-pot and two-pot protocols were compared, no significant differences concerning the stereocontrol were found, so the advantages of the one-pot procedure are clear. Copyright

CAMPHOR-DERIVED COMPOUNDS, METHOD FOR MANUFACTURING THE SAME, AND APPLICATION THEREOF

Camphor-derived compounds are disclosed, which are represented as the following formula (I): wherein R1, R2, R3, and R4 each are defined as described in the specification. In addition, a method for manufacturing the camphor-derived compounds and application thereof are disclosed.

Enantioselective addition of dialkylzincs to aldehydes catalyzed by (-)-MITH

An effective catalytic system that imparts high enantioselectivity has been disclosed for the synthesis of optically active alcohols, which may undergo further chemical transformations. The enantioselective alkylation of aldehydes with dialkylzincs to afford the corresponding optically active alcohols with excellent enantioselectvities has been achieved in the presence of 0.1-0.5 mol % of the camphor-derived chiral ligand (-)-2-exo-morpholinoisobornane-10-thiol (MITH) (1) at room temperature or at 0 °C. I zinc so too: The enantioselective alkylation of aldehydes with dialkylzincs yielded the desired alcohol products with up to 99 % ee in the presence of 0.1-0.5 mol % of ligand (-)-2-exo-morpholinoisoborne-10-thiol (1) at room temperature or at 0°C. Copyright

CuH-catalyzed enantioselective 1,2-reductions of α,β-unsaturated ketones

The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.

Perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as ligands for the catalytic enantioselective addition of diethylzinc to aldehydes

The catalytic potency of a series of perhydro-1,3-benzoxazines prepared from (-)-8-aminomenthol was examined in the enantioselective addition of diethylzinc to aldehydes. When (2R,3S,3aS,4aR,6R,8aS)-2-isopropyl-6,9,9- trimethyl-3-phenyldecahydro-4aH-pyrrolo[2,1-b][1,3]benzoxazin-3-ol 7b was used as a chiral ligand, 1-substituted propanols with an (R)-configuration were obtained in high yields and enantiomeric excesses up to >99%. The catalyst can be recovered and used without any loss in its activity.

Enantioselective ethylation of aldehydes using a regenerable polymer-supported N-picolylvalinol tridentate ligand

A supported pyridine-based tridentate chiral ligand has been prepared and evaluated for enantioselective addition of diethylzinc to aldehydes. The catalyst allowed the preparation of various chiral alcohols with the R configuration in good yields and enan

Polystyrene-supported (R)-2-piperazino-1,1,2-triphenylethanol: A readily available supported ligand with unparalleled catalytic activity and enantioselectivity

(Chemical Equation Presented) A very active and highly enantioselective catalytic resin, designed for minimal perturbation of the catalytic center by the polymer matrix, has been assembled in two steps from (S)-triphenylethylene oxide, piperazine, and Merrifield resin and tested in the enantioselective ethylation of aldehydes. 1-Arylpropanols of 94-95% ee are obtained in high yield by the use of only 2 mol % of catalytic resin at 0°C for 4 h.

Highly enantio- and diasfereoselective one-pot synthesis of acyclic epoxy alcohols with three contiguous stereocenters

Two highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols with up to three contiguous stereocenters are reported. Route one involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselect