vic-Functionalized amines are well represented in numerous bioactive natural products and pharmaceuticals as well as being essential building blocks in organic synthesis, drug design, and material science. Herein, we report the direct bis-functionalization of olefins utilizing N-methyl-O-tosylhydroxylamine (TsONHMe) in the presence of a di-rhodium catalyst and a nucleophile in CH3CN. This unprecedented process installs an N-methylamine and another moiety including hydroxy, methoxy, or azide. The scope and mechanism will be discussed. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/240nm/uploads/45476_aa-acsabstract2010-fig1.jpg' alt='' />

Bis-functionalization of olefins: Direct synthesis of bis-functionalized amines

247th National Meeting (2014)

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