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C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels–Alder reactions

✍ Scribed by Yuanhui Ma; Yong Jian Zhang; Shangbin Jin; Qiqi Li; Chenguang Li; Junseong Lee; Wanbin Zhang

Book ID
104097083
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
402 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new class of C 2 -symmetric 3,3 0 -dialkoxy-2,2 0 -bipyrrolidines have been designed and developed for asymmetric organocatalytic Diels-Alder reactions of a,b-unsaturated aldehydes. The bipyrrolidines combined with HClO 4 were found to be effective organocatalysts for enantioselective Diels-Alder reactions. The catalysis mode has been demonstrated by NMR and X-ray crystallographic studies for diiminium intermediate.

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✍ Takato Mitsudome; Kenta Nose; Tomoo Mizugaki; Koichiro Jitsukawa; Kiyotomi Kaned 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 168 KB

A chiral organocatalyst was successfully entrapped by montmorillonite clay using the cation-exchange method. The mont-entrapped organocatalyst acted as a highly efficient and reusable heterogeneous catalyst for the asymmetric Diels-Alder reaction, without loss of its initial activity.