83976-52-7Relevant academic research and scientific papers
Asymmetric Michael Additions. Stereoselective Alkylations of the (R)- and (S)-Enamine from Cyclohexanone and 2-(Methoxymethyl)pyrrolidine by Methyl α-(Methoxycarbonyl)cinnamates
Blarer, Stefan J.,Seebach, Dieter
, p. 2250 - 2260 (2007/10/02)
Alkylation of (2S)-1-(1-cyclohexen-1-yl)-2-(methoxymethyl)pyrrolidine ((S)-1, enamine from cyclohexanone and 2-(methoxymethyl)pyrrolidine) by the Knoevenagel condensation products 4 of aromatic aldehydes yields 35-76percent of Michael adducts (1 + 4 -> ->
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
Blarer, Stefan J.,Schweizer, W. Bernd,Seebach, Dieter
, p. 1637 - 1654 (2007/10/02)
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.
