108735-31-5Relevant academic research and scientific papers
Enantioselective construction of cyclic ethers by an aldol-cyclization sequence
Galatsis, Paul,Millan, Scott D.,Ferguson, George
, p. 5048 - 5056 (2007/10/03)
We have modified the substrate used in deconjugative aldol-cyclizations by incorporating the Evans chiral auxiliary. The deconjugative aldol step, using boron enolates, gave the expected products with complete syn-aldol stereochemistry. These compounds could then undergo an iodine-mediated cyclization to form optically active products. Oxetanes and fused ring tetrahydrofurans were easily assembled with a variety of substitutiion patterns and with excellent enantiocontrol. The deconjugation of acyclic chiral enimides resulted in the loss of control of olefin geometry. However, these compounds did appear to cyclize with excellent enantiocontrol.
ALDOL ADDITION REACTIONS OF CHIRAL CROTONATE IMIDES
Evans, David A.,Sjogren, Eric B.,Bartroli, Javier,Dow, Robert L.
, p. 4957 - 4960 (2007/10/02)
Aldol addition reaction of the crotonate imides 1 and 2 affords the adducts 3 and 4 with high diastereoselection.Subsequent removal of the chiral auxiliary can be effected in good yield to provide a number of synthetically useful intermediates.
