Domino Michael/Mannich Annulation Reaction of N-Sulfinyl Lithiodienamines
- 2 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7014-7017
- https://doi.org/10.1021/acs.orglett.1c02201
Abstract
The domino Michael/Mannich (DMM) annulation reaction between an N-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 with diastereomeric ratios as high as >19:1.Funding Information
- Division of Chemistry (CHE-1665145)
- Temple University
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