Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation

Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation
Amy A. Ott, Joseph J. Topczewski, Charles S. Goshey
The catalytic enantioselective preparation of densely functionalized amines is a fundamental synthetic challenge. To address this challenge, we report for the first time that the Winstein rearrangement can be enlisted as the racemization pathway in a dynamic kinetic resolution of allylic azides. Alkene functionalization by Sharpless dihydroxylation affords tertiary azides in excellent enantioselectivity (up to 99:1 er). This approach establishes the chirality of the tertiary azide, obviates the need to directly forge either a congested C–N or C–C bond at the new nitrogenous stereocenter, and establishes additional functionality. Several examples demonstrate further elaboration of this functionality.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04203

DOI: 10.1021/jacs.7b04203

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