Recyclable Organocatalyst-Promoted One-Pot Asymmetric Synthesis of Spirooxindoles Bearing Multiple Stereogenic Centers

A recyclable fluorous bifunctional Cinchona alkaloid/thiourea‐catalyzed and four‐component Michael/Mannich/cyclization sequence has been developed for the asymmetric synthesis of spirooxindoles containing 2‐piperidinone and tetrahydropyridine rings. This one‐pot reaction process affords the products...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-12, Vol.357 (18), p.3820-3824
Main Authors: Huang, Xin, Pham, Kenny, Yi, Wenbin, Zhang, Xiaofeng, Clamens, Cécilia, Hyatt, Jeremy H., Jasinsk, Jerry P., Tayvah, Uriel, Zhang, Wei
Format: Article
Language:English
Subjects:
Alkaloids
asymmetric catalysis
Asymmetry
Bearing
Catalysis
Chemical Sciences
Direct reduction
one-pot reaction
organocatalysis
recyclable organocatalyst
spirooxindoles
Synthesis
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Summary:A recyclable fluorous bifunctional Cinchona alkaloid/thiourea‐catalyzed and four‐component Michael/Mannich/cyclization sequence has been developed for the asymmetric synthesis of spirooxindoles containing 2‐piperidinone and tetrahydropyridine rings. This one‐pot reaction process affords the products in good to excellent yields and up to 99% ee and 9:1 dr.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500748