98223-52-0Relevant academic research and scientific papers
Stereoselective alkylations in rigid systems. Effect of remote substituents on π-facial additions to lactam enolates. Stereoelectronic and steric effects
Meyers,Seefeld, Mark A.,Lefker, Bruce A.,Blake, James F.,Williard, Paul G.
, p. 7429 - 7438 (2007/10/03)
A series of chiral bicyclic lactams has been studied by both experiment and ab initio molecular orbital calculations, The facial selectivity of the alkylation of their enolates shows a high degree of endo or exo entry, depending upon certain substituents and their positions in the lactams. The suggested reasons for the exo or endo selectivity for alkylation were determined to be purely electronic or purely steric in certain instances, The results of the selectivity study now allow the asymmetric synthesis of various ketones, acids, and pyrrolidines in either enantiomeric form based on the choice of lactam employed.
CHIRAL QUATERNARY CARBON COMPOUNDS. II. AN ASYMMETRIC SYNTHESIS OF (R) OR (S)-4,4-DIALKYL-2-CYCLOPENTENONES.
Meyers, A. I.,Wanner, Klaus Th.
, p. 2047 - 2050 (2007/10/02)
The chiral bicyclic lactam (5) derived from levulinic acid and (S)-valinol is sequentially alkylated and then cleaved to 2,2-dialkyl levulinaldehyde (8) which is cyclized to the title products (9) in > 99percent ee.
