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

Xin Huang (1) , Kenny Pham (1) , Wenbin Yi (2) , Xiaofeng Zhang (1) , Cécilia Clamens (3) , Jeremy H. Hyatt (1) , Jerry P. Jasinsk , Uriel Tayvah (4) , Wei Zhang (1)

1 UMass Amherst - University of Massachusetts [Amherst]
2 NJUST - Nanjing University of Science and Technology
3 ISCR - Institut des Sciences Chimiques de Rennes
4 Princeton University

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

Keywords: one-pot reaction; asymmetric catalysis; recyclable organocatalyst; spirooxindoles; organocatalysis

Domains: Chemical Sciences

Xin Huang, Kenny Pham, Wenbin Yi, Xiaofeng Zhang, Cécilia Clamens, et al.. Recyclable Organocatalyst-Promoted One-Pot Asymmetric Synthesis of Spirooxindoles Bearing Multiple Stereogenic Centers. Advanced Synthesis and Catalysis, 2015, 357 (18), pp.3820-3824. ⟨10.1002/adsc.201500748⟩. ⟨hal-01242906⟩