83976-41-4

Upstream product

• 63126-47-6 (2S)-2-(methoxymethyl)-1-pyrrolidine 
• 108-94-1 cyclohexanone 

Downstream Products

• 86661-26-9 2-[(R)-Benzo[1,3]dioxol-5-yl-((S)-2-oxo-cyclohexyl)-methyl]-malonic acid dimethyl ester 
• 86661-26-9 2-[(R)-Benzo[1,3]dioxol-5-yl-((R)-2-oxo-cyclohexyl)-methyl]-malonic acid dimethyl ester 
• 86661-26-9 (-)-(1'S,1''S)<(1,3-Benzodioxol-5-yl)(2-oxocyclohexyl)methyl>propandisaeure-dimethylester 
• 83976-44-7 (S)-2-((R)-1-(4-chlorophenyl)-2-nitroethyl)cyclohexanone 
• 127222-88-2 (S)-1-(7-Benzenesulfonyl-1,3,4,5,8,8a-hexahydro-2H-naphthalen-4a-yl)-2-methoxymethyl-pyrrolidine 
• 101328-16-9 (+)-(2R,3S)-3-nitro-2-phenylbicyclo<3.3.1>nonan-9-one 
• 101694-77-3 (+)-menthyl (1'S,2R)-2-benzoylamino-2-(2-oxocyclohexyl)acetate 
• 15409-60-6 2-(Dimethylaminomethyl)-1-cyclohexanon 
• 138060-83-0 2-(Dimethylaminomethyl)-1-cyclohexanon 
• 253609-29-9 (1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]cyclohexanone 
• 24738-84-9 S-2-<2-(carbomethoxyl)ethyl>cyclohexanone 

Relevant academic research and scientific papers

Enantioselective telomerization 1. Telomerization of butadiene with formaldehyde, β-dicarbonyl compounds, nitroalkanes, and enamines

Enantioselective telomerization reactions catalyzed by homogeneous palladium catalysts are described.Applying the concept of chiral bidentate phosphorus ligands and low temperatures proved useful in telomerizing butadiene with formaldehyde, with a β-dicarbonyl compound and with a nitroalkane.Excess of enantiomers up to 41percent could be obtained.With a chiral enamine as nucleophile ee values of 72percent have been observed.

Asymmetric induction in stereoselective carbocyclization of cyclohexanone enamines

A highly enantioselective synthesis of bicyclo[3.3.1 ]nonane diketones 3-5 was accomplished by (S)- and (R)-2-methoxymethylpyrrolidine induced asymmetric cyclization of cyclohexanone enamines 1,2 in reaction with propenoyl chloride. A possible enantiodifferentiation reaction mechanism was suggested.

Stereocontrolled Syntheses of Mannich Bases and γ-Amino Alcohols

The reaction of enantiomerically pure SMP enamines 2 with iminium tetrachloroaluminates 3 yields optically active Mannich bases 4.Diastereoselective reduction of 4 gives γ-amino alcohols 5 with the desired configuration. Key Words: Mannich bases / Enamines / Iminium salts / γ-Amino alcohols

2-PHENYLSULFONYL 1,3-DIENES IN ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ENAMINES AND ENOL ETHERS

2-Phenylsulfonyl 1,3-dienes underwent diastereoselective inverse electron demand Diels-Alder reactions with enamines (up to 73percent de) and enol ethers (up to 50percent de).

Asymmetrische Michael-Additionen. Praktisch vollstaendig diastereo- und enantioselective Alkylierungen des Enamins aus Cyclohexanon und Prolinylmethylaether durch ω-Nitrostyrole zu u-2-(1'-Aryl-2'-nitroaethyl)cyclohexanonen

When the enamine (S)-N-(1'-cyclohexenyl)-2-methoxymethyl-pyrrolidine is added to 2-aryl-1-nitroethylenes, only one of the four possible enantiomerically pure diastereomers is formed.Hydrolysis of the crude primary products furnishes α-alkylated cyclohexanones of >90percent e.e. (3, Scheme 3).Their (2S,1'R)-configuration was deduced by chemical correlation with 1-cyclohexyl-1-phenyl-ethane and from an X-ray crystal structure analysis of (-)-(2R,3S,6'R,1''S)-3-methyl-N--2-phenylmorpholine (11a, Scheme 5 and Fig. 2). - The relative topicity of reactant approach with the prolinol derivative (see II) is specified as 1k,ul-1,4.The steric course and the mechanism of the reaction are discussed.