Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines

Villar, Laura; Orlov, Nick; Kondratyev, Nikolay S.; Uria, Uxue; Vicario, Jose L.; Malkov, Andrei

Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines

journal contribution

posted on 2018-09-11, 14:08 authored by Laura Villar, Nick Orlov, Nikolay S. Kondratyev, Uxue Uria, Jose L. Vicario, Andrei MalkovAndrei Malkov

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.

Funding

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.

History

School

Science

Department

Chemistry

Published in

Chemistry - A European Journal

Citation

VILLAR, L. ... et al, 2018. Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines. Chemistry: a European journal, 24 (61), pp.16262-16265.

Publisher

Version

AM (Accepted Manuscript)

Publisher statement

"This is the peer reviewed version of the following article: VILLAR, L. ... et al, 2018. Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines. Chemistry: a European journal, 24 (61), pp.16262-16265, which has been published in final form at https://doi.org/10.1002/chem.201804395. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.