Hydrostannylation-cross-coupling strategy for the stereoselective synthesis of alkylidenemalonates and related α,β-unsaturated esters
A method for the stereoselective synthesis of alkylidenemalonates and related α,β-unsaturated esters by a hydrostannylation-cross-coupling process has been developed. Pd-catalyzed and radical hydrostannylation of propiolate derivatives stereoselectively provided α-alkoxycarbonyl (E)- and (Z)-vinylstannanes, respectively, which were then converted into alkylidenemalonates by the Stille coupling reaction. A one-pot process was also realizable for the Pd-catalyzed reactions.
Thermal Cycloaddition Reactions of ?-Delocalized Singlet Vinylcarbenes: Three-Carbon 1,1-/1,3-Dipoles. The Thermal Three-Carbon + Two-Carbon Cycloaddition
Full details of investigations defining new aspects of the scope and mechanism of the three-carbon + two-carbon cycloaddition reaction of ?-delocalized singlet vinylcarbenes (three-carbon 1,1-/1,3-dipoles generated in a reversible, thermal ring opening of cyclopropenone ketals) are detailed.
Boger, Dale L.,Wysocki, Ronald J.
p. 3408 - 3421
(2007/10/02)
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