Diastereo‐ and Enantioselective Synthesis of Spiro‐Pyrrolidine‐Pyrazolones by Squaramide‐Catalyzed Cascade Aza‐Michael/Michael Reactions | Zendy

Li JunHua | Zendy; Wen Hongliang | Zendy; Liu Lei | Zendy; Du DaMing | Zendy

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Diastereo‐ and Enantioselective Synthesis of Spiro‐Pyrrolidine‐Pyrazolones by Squaramide‐Catalyzed Cascade Aza‐Michael/Michael Reactions

Author(s) -

Li JunHua,

Wen Hongliang,

Liu Lei,

Du DaMing

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600316

Subject(s) - squaramide , pyrrolidine , chemistry , michael reaction , bifunctional , enantioselective synthesis , cascade reaction , diastereomer , pyrazolones , organocatalysis , catalysis , organic chemistry , stereochemistry

A new method was developed to rapidly generate a series of spiro‐pyrrolidine‐pyrazolones by using a squaramide‐catalyzed cascade aza‐Michael/Michael addition of either tosylaminomethyl enones or enoates to unsaturated pyrazolones. This tandem reaction sequence proceeded well by using 5 mol‐% of a chiral bifunctional tertiary amine squaramide catalyst to afford the desired products in good to excellent yields (up to 98 %) with excellent diastereoselectivities [up to >20:1 diastereomeric ratio ( dr )] and high to excellent enantioselectivities (up to 98 % ee ).

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