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Issue 33, 2019
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Iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide by the use of a borrowing hydrogen methodology

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Abstract

An iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide was developed under basic conditions, affording the optically active secondary sulfinamides in high yields and diastereoselectivities. The removal of the sulfinyl group from sulfonamides allowed a facile access to a wide range of α-chiral primary amines. This synthetic strategy was further applied in the synthesis of the marketed pharmaceuticals (S)-rivastigmine and NPS R-568.

Graphical abstract: Iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide by the use of a borrowing hydrogen methodology

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Publication details

The article was received on 25 Jun 2019, accepted on 18 Jul 2019 and first published on 19 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01417A
Org. Biomol. Chem., 2019,17, 7651-7654

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    Iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide by the use of a borrowing hydrogen methodology

    X. Xi, Y. Li, G. Wang, G. Xu, L. Shang, Y. Zhang and L. Xia, Org. Biomol. Chem., 2019, 17, 7651
    DOI: 10.1039/C9OB01417A

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