Asymmetric synthesis of amino-benzothiazol derivatives by additions of 2-lithiated benzothiazoles to (S)-N-t-butylsulfinyl-ketiminesElectronic supplementary information (ESI) available: Experimental procedures, full spectroscopic data for compounds 8-10 and copies of 1H NMR and 13C NMR spectra. CCDC 1024268. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ra15405c

• Main Authors: Dai, Yanling, Xie, Chen, Wu, Lingmin, Mei, Haibo, Soloshonok, Vadim A, Han, Jianlin, Pan, Yi
• Format: Journal Article
• Language: English
• Published: 11.12.2014
• ISSN: 2046-2069
• DOI: 10.1039/c4ra15405c

The reactions between lithium-benzothiazoles and ( S )- N-tert -butanesulfinylketimines have been found to be of general synthetic importance for asymmetric preparation of previously unknown type of amino-benzothiazol derivatives of high pharmaceutical potential. In most cases, the reactions proceed with excellent diastereoselectivities and good isolated yields of the target compounds rendering the developed procedure of high synthetic value and immediate practical use. We reported the asymmetric Mannich reactions between lithium-benzothiazoles and ( S )- N-tert -butanesulfinylketimines, which gave unknown type of amino-benzothiazol derivatives of high pharmaceutical potential with up to 96% yields and 99 : 1 diastereoselectivities.