High-pressure-assisted addition of (methoxyphenyl)maleic anhydrides to dienes. Synthesis of 3a-aryltetrahydroisoindole-1,3-diones
A new synthesis of (2-and 4-methoxyphenyl)maleic anhydrides was accomplished, the reactions of which with cyclopentadiene and 3-sulfolene, serving as a 1,3-butadiene equivalent, furnished the [4+2]-cycloadducts. The latter were converted into imides of 2-
Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides
Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides were hydrogenated well to provide the desired products 3-substituted succinic anhydrides in one hour with excellent results (full conversions, up to 99% yield, 99% ee, 3000 TON). Importantly, we developed a creative and efficient synthetic route to construct the key intermediate of the hypoglycemic drug mitiglinide through our catalytic system.
Arylmaleic anhydrides via Heck arylation of fumaric acid
Palladium-catalyzed arylation of fumaric acid with aryl iodides is found to be a very simple, economic and scalable approach to arylmaleic anhydrides. The reaction is facilitated by the presence of donor moieties on the aryl fragment and does not occur wi
Roshchin, Alexander I.
experimental part
p. 3633 - 3635
(2010/08/13)
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