Organic Letters
Organic Letters
5 years ago

Role of Configuration at C6 in Catalytic Activity of l-Proline-Derived Bifunctional Organocatalysts

Role of Configuration at C6 in Catalytic Activity of l-Proline-Derived Bifunctional Organocatalysts
Do Hyun Ryu, Soo Min Cho, Hui Jin, Juyeol Lee
l-Proline-derived chiral bifunctional (thio)urea organocatalysts epi-PTU and epi-PU were newly synthesized, and their catalytic performances were compared with their C6 epimeric catalysts PTU and PU in various Michael reactions of nitrostyrene in terms of reactivities and stereoselectivities. The experimental results indicate that a proper relative stereochemistry at C2 and C6 in l-proline-derived bifunctional organocatalysts is important for successful catalysis and that catalysts (PTU and PU) with the 2S,6R configuration are much more efficient.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01000

DOI: 10.1021/acs.orglett.7b01000

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