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Synfacts 2009(2): 0158-0158  
DOI: 10.1055/s-0028-1087498
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Everything’s Coming Up Rosamine

Contributor(s): Timothy M. Swager, Eric L. Dane
L. Wu, K. Burgess*
Texas A&M University, College Station, USA
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Ditriflate 1 is converted into ros­amine precursors 2 via a double SNAr addition of cyclic amines in DMSO. The reaction can be run stepwise to obtain unsymmetrically substituted products in high yield. A variety of aryllithium and aryl-Grignard reagents can react with 2 to form ­rosamines 3 in high yield. The conversion of 4 to 6 via two high-yielding steps further illustrates the utility of this synthetic method.