1 research outputs found
Exploring the Steric and Electronic Factors Governing the Regio- and Enantioselectivity of the Pd-Catalyzed Decarboxylative Generation and Allylation of 2‑Azaallyl Anions
The impact of the steric and electronic
factors in both the <i>para</i>-substituted benzaldimine
and 2,2-diarylglycine components
on the regioselectivity and enantioselectivity of the palladium-catalyzed
decarboxylative allylation of allyl 2,2-diarylglycinate aryl imines
was explored. These studies revealed that using 2,2-diÂ(2-methoxyphenyl)Âglycine
as the amino acid linchpin allowed for the exclusive synthesis of
the desired homoallylic benzophenone imine regioisomers, independent
of the nature of the imine moiety, in typically high yields. The resulting
enantiomeric ratios, however, are slightly decreased in comparison
to the transformations involving the corresponding allyl 2,2-diphenylglycinate
imines, but this is more than balanced out by the increases in yield
and regioselectivity. Overall, these studies suggest a general strategy
for the highly regioselective functionalization of 2-azaallyl anions