Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines
journal contributionposted on 11.09.2018 by Laura Villar, Nick Orlov, Nikolay S. Kondratyev, Uxue Uria, Jose L. Vicario, Andrei Malkov
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Highly enantioenriched, chromatographically stable secondary allylboronates derived from 1,1,2,2‐tetraethyl‐1,2‐ethanediol were obtained by kinetic resolution of their racemic mixtures. The resolved reagents were applied in stereoselective synthesis of homoallylic amines with an internal double bond employing unprotected imines formed in situ from aldehydes and ammonia. The reactions proceeded with an excellent transfer of chirality.
We thank the Leverhulme Trust for the Research grant RGP-2015-351. Spanish MINECO (FEDER-CTQ2017-83633-P and FPI-BES-2012-051856 fellowship to L.V.) and Basque Government (IT908-16), are also gratefully acknowledged.