790702-61-3Relevant academic research and scientific papers
A high yielding route to substituted piperidines via the aza-Diels-Alder reaction
Bailey, Patrick D,Smith, Peter D,Pederson, Frederick,Clegg, William,Rosair, Georgina M,Teat, Simon J
, p. 1067 - 1070 (2002)
The imine Ph2CHN=CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, is an excellent dienophile in aza-Diels-Alder reactions, giving diastereomerically pure cycloadducts in high yield.
Synthesis of an advanced intermediate en route to the mitomycin natural products
Williams, Amie L.,Srinivasan, Jayasree M.,Johnston, Jeffrey N.
, p. 6047 - 6049 (2007/10/03)
(Chemical Equation Presented) An advanced intermediate in our planned synthesis of mitomycin C has been acquired in nine steps from tert-butyl glyoxylate. The aziridinyl pyrrolidine and quinone subunits are coupled regioselectively to arrive at an enamine
Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions
Brunner, Bernhard,Stogaitis, Nicole,Lautens, Mark
, p. 3473 - 3476 (2007/10/03)
The application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-α,β-unsaturated aldehyde, followed by isomerization to the (Z)-isomer, cyclization, and elimination of a water molecule, leading to the formation of the 1,2-dihydropyridine.
Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement of Vinyloxiranes
Lautens, Mark,Tayama, Eiji,Nguyen, Duy
, p. 345 - 347 (2007/10/03)
(Matrix presented) The first synthetic application of 2-methyl-2- vinyloxirane as a masked dienolate has been successfully demonstrated in the direct vinylogous Mannich-type reaction with an α-imino ester as an electrophile. The Mannich adduct was a usefu
