A silver/base catalyst system was
developed to effectively activate alkyne derivatives to capture CO2. We reported
that the combined use of a catalytic amount of silver acetate and DBU
efficiently catalyzed the incorporation of CO2 under mild reaction conditions
for a wide range of propargyl alcohols to afford the corresponding cyclic
carbonates in high-to-excellent yields. This procedure can be applied to various
alkyne containing substrates to afford the corresponding heterocycles. In this
reaction, the corresponding α, β-unsaturated carbonyl compounds generated via a
decarboxylative Meyer-Schuster type reaction were realized in some polar
solvents, such as form amides. Recently, we reported the
decarboxylative Nazarov type reaction to afford the highly substituted
2-cyclopentenones from the corresponding cyclic carbonate, prepared with the
silver-catalyzed CO2 incorporation into propargyl alcohol derivatives. When the
carbonate was treated with a catalytic amount of BF3•OEt2 in 1, 2-dichloroethane
at room temperature, the Nazarov cyclization proceeded to afford
trans-2-cyclopentenones with high stereoselectivity and in high yield. 8 This
procedure can be applied to the chirality transfer system to afford the
corresponding 2-cyclopentenones in optically pure form.
个人简介
Prof. Tohru Yamada's research
include new synthetic reactions catalyzed by metal complexes, e.g. catalytic
enantioselective reduction, carbon dioxide fixation for organic synthesis, and
microwave application to organic synthesis.
前往“发现”-“看一看”浏览“朋友在看”