Two generations of stereoselective synthesis of 1,3-diamino-2-ols are described. Each synthesis proceeds through the Rh-catalyzed aziridination of an allenic carbamate to form a bicyclic methylene aziridine (MA). In the first generation synthesis, a second aziridination of the MA forms a 1,3-Diazaspiro-[2.2]-pentane (DASP) structure, which undergoes acetate ring-opening and acid-catalyzed rearrangment to form a 1,3-diaminated ketone. In the second generation synthesis, this ketone is accessed directly via regioselective aminohydroxylation of the MA. Stereoselective reduction of the ketones yields the desired 1,3-diamino-2-ols.

New methods for the stereoselective synthesis of 1,3-diamino-2-ols via allene oxidation

245th National Meeting (2013)

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