Construction of Acyclic All-Carbon Quaternary Stereocenter Based on Asymmetric Michael Addition of Chiral Amine

Acyclic asymmetric quaternary stereocenters, which are composed of four carbon-carbon bonds, were finely constructed by utilizing a face-selective alkylation enolate intermediates derived from an Michael addition reaction chiral lithium amide with trisubstituted (E)-α,β-unsaturated esters. The present was able to employ diverse alkyl halides as electrophile afford various adducts having all-carbon stereocenter. With regard the deprotection auxiliary, N-iodosuccinimide used in our previous study did not work cases; however, we found that pyridine iodine monochloride presence H2O effective remove bornyl group and benzyl on amino provide β-amino ester derivative.