Abstract
A new and efficient synthetic method to obtain fully-substituted hexahydroisoindolinones was developed by using bifunctional tertiary amine-thioureas as powerful catalysts. As far as we know, there is no efficient synthetic method developed toward fully-substituted hexahydroisoindolinones. The products were obtained in good yield and diastereoselectivity. The one-pot cascade quadruple protocol features readily available starting materials, simple manipulation, mild conditions and good atom economy.
Highlights
Isoindolines and their congeners are one kind of the most widespread compounds in nature
It is highly desirable to develop efficient methods toward the synthesis of isoindoline derivatives, which is a frontier in organic synthesis
The first method was the synthesis of 3-substituted isoindolinones from the corresponding N-methylmaleimides by the Diels–Alder reaction with 1,3-butadiene followed by hydrogenation
Summary
Isoindolines and their congeners are one kind of the most widespread compounds in nature. To the best of our knowledge, no efficient method toward the synthesis of fully-substituted hexahydroisoindolinones has been developed so far. After 12 h at room temperature, the reaction afforded the expected product rac-3a in 59% yield (Table 1, entry 1). When Et3N was used, the reaction afforded the product with 41% yield (Table 1, entry 2).
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