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Enantioselective Synthesis of Janus Kinase Inhibitor INCB018424 via an Organocatalytic Aza-Michael Reaction

✍ Scribed by Lin, Qiyan; Meloni, David; Pan, Yongchun; Xia, Michael; Rodgers, James; Shepard, Stacey; Li, Mei; Galya, Laurine; Metcalf, Brian; Yue, Tai-Yuen; Liu, Pingli; Zhou, Jiacheng


Book ID
121429756
Publisher
American Chemical Society
Year
2009
Tongue
English
Weight
228 KB
Volume
11
Category
Article
ISSN
1523-7060

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Enantioselective Synthesis of Janus Kina
✍ Lin, Qiyan; Meloni, David; Pan, Yongchun; Xia, Michael; Rodgers, James; Shepard, πŸ“‚ Article πŸ“… 2009 πŸ› American Chemical Society 🌐 English βš– 228 KB

An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and