83976-49-2

Upstream product

• 5153-67-3 nitrostyrene 
• 83976-43-6 (2R,3S)-N-(1'-Cyclohexenyl)-3-methyl-2-phenylmorpholin 
• 84025-82-1 (-)-(2R,3S)-3-Methyl-2-phenylmorpholin 
• 108-94-1 cyclohexanone 

Downstream Products

• 84025-87-6 (-)-(2S,1'S)-2-(2'-Nitro-1'-phenylaethyl)cyclohexanon 
• 4591-64-4 (R)-2-((S)-2-nitro-1-phenylethyl)-cyclohexanone 

Relevant academic research and scientific papers

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.