Abstract

An efficient asymmetric Michael/cyclization cascade reaction of 4-chromanones with isothiocyanato oxindoles has been revealed. Under bifunctional organocatalysis by rosin-based squaramide catalyst, a series of spiro[oxindole/thiobutyrolactam/chromanone] complexes were conveniently constructed in a highly stereoselective manner (up to 99% yields, > 20:1 dr and >99% ee). The reaction leads to the formation of three contiguous stereogenic centers and two spiro quaternary stereocenters.

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