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. 2008 Aug 27;130(34):11248-9.
doi: 10.1021/ja803344v. Epub 2008 Aug 5.

Catalytic C-H amination for the preparation of substituted 1,2-diamines

David E Olson  1 , J Du Bois
Affiliations

Catalytic C-H amination for the preparation of substituted 1,2-diamines

David E Olson et al. J Am Chem Soc. .

Abstract

Rhodium-catalyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique oxathiadiazinane heterocycles, which upon mild reduction furnish differentially substituted 1,2-diamine products. This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction.

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Figures

Figure 1
Figure 1
A two-step protocol for the preparation of 1,2-diamines.
Figure 2
Figure 2
Reductive N—O cleavage furnishes 1,2-diamine derivatives. Products purified by HPLC using H2O/CH3CN/CF3CO2H.
See this image and copyright information in PMC

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