497161-72-5Relevant academic research and scientific papers
Iron(III) 2-ethylhexanoate as a novel, stereoselective hetero-Diels-Alder catalyst
Gorman, David B.,Tomlinson, Ian A.
, p. 25 - 26 (1998)
Iron(III) 2-ethylhexanoate has been used as a novel, mild Lewis acid catalyst for the stereoselective Diels-Alder reaction of ethyl (E)-4-oxobutenoate with alkyl vinyl ethers to stereoselectively produce cis-2-alkoxy-3,4-dihydro-2H-pyran-4-carboxylic acid, ethyl esters with diastereoisomeric excesses (de) as high as 98%.
Highly enantioselective inverse-electron-demand hetero-Diels-Alder reactions of α,β-unsaturated aldehydes
Gademann, Karl,Chavez, David E.,Jacobsen, Eric N.
, p. 3059 - 3061 (2007/10/03)
Straightforward access to useful synthetic intermediates is provided by this new method. Simple, α,β-unsaturated aldehydes are excellent substrates in the hetero-Diels-Alder reaction with inverse electron demand, catalyzed by CrIII-Schiff base complexes (see scheme; R1, R2 = alkyl or aryl) in the presence of 4-A molecular sieves and no solvent. The resulting dihydropyrans are obtained in high enantio- (89-98 % ee) and diastereoselectivity (> 95 % de) and yield (40-95 %).
