Stereochemistry AbstractTo create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. You may insert more abstracts by copying this box or by using the menu option to insert a stereochemistry abstract.
Abstract:The asymmetric 1,3-dipolar cycloaddition (1,3-DC) of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to perform the synthesis of enantiomerically enriched key structure to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed employing different imino esters and dipolarophiles, and furtherly compared with the same cycloaddition reactions performed with chiral phosphoramidite 14·Ag(I) complex.
The multicomponent Amine-Aldehyde-Dienophile reaction is optimized employing benzyl or 4methoxybenzylamine. The interest of the transformation consist in synthesis of polysubstituted cyclohex-2-enylamines. The study of the scope of this AAD process is carried out as well as the diastereoselective version employing commercially available chiral benzylic amines and a maleimide with the chiral information at the N-substituent. VCD spectroscopy is a very useful tool for the determination of the absolute configuration of the isolated enantiomerically enriched compounds.
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