Synthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocentersviaan Organocatalytic Asymmetric Tandem Michael-Henry Reaction

Autor: Zhenghong Zhou, Youming Wang, Liang-Fu Tang, Lulu Wu, Haibin Song, Chuchi Tang
Rok vydání: 2013
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 355:1053-1057
ISSN: 1615-4150
DOI: 10.1002/adsc.201300086
Popis: Optically active 2H-thiopyrano[2,3-b]quinolines with three contiguous stereocenters have been synthesized via a chiral bifunctional squaramide-catalyzed tandem Michael–Henry reaction between 2-mercaptoquinoline-3-carbaldehydes and nitroolefins. The reactions proceed with excellent diastereo- and enantioselectivity to give the title compounds in high yields with high levels of diastereo- and enantioselectivity (up to >99/1 dr and >99% ee, respectively).
Databáze: OpenAIRE
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