The domino Michael/Mannich (DMM) annulation reaction between an <i>N</i>-sulfinyl lithiodienamine and an electrophilic alkene is developed for the synthesis of chiral 2-amino cyclohexenes, a key building block in asymmetric synthesis. The DMM reaction proceeds at low temperature while maintaining the stereochemical fidelity. The product functionalized amino cyclohexenes, here obtained in 55-82% yield and diastereomeric ratios as high as &gt;19:1.

Domino Michael/Mannich reaction of <i>N</i>-sulfinyl metallodienamines

ACS Spring 2022

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Domino Michael/Mannich reaction of N-sulfinyl metallodienamines