Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation

Amy A. Ott, Charles S. Goshey, Joseph J. Topczewski

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)7737-7740
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number23
DOIs
StatePublished - Jun 14 2017

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