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Jin X , Chatare VK , Yu PC , Gau MR , O'Sullivan OT , Andrade RB
Domino Michael/Mannich Annulation Reaction of N-Sulfinyl Lithiodienamines
Org Lett. 2021 Sep 17;23(18) :7014-7017
PMID: 34473521   
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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.
Notes
1523-7052 Jin, Xiao Orcid: 0000-0002-5423-0982 Chatare, Vijay K Yu, Po-Cheng Gau, Michael R O'Sullivan, Owen T Andrade, Rodrigo B Orcid: 0000-0002-4554-8323 Journal Article United States Org Lett. 2021 Sep 17;23(18):7014-7017. doi: 10.1021/acs.orglett.1c02201. Epub 2021 Sep 2.