497161-76-9Relevant articles and documents
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 %).