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Title: Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines
Authors: Villar, Laura
Orlov, Nikolai V.
Kondratyev, Nikolay S.
Uria, Uxue
Vicario, Jose L.
Malkov, Andrei V.
Keywords: Asymmetric synthesis
Allylation
Amines
Kinetic resolution
Stereoselectivity
Issue Date: 2018
Publisher: © Wiley
Citation: VILLAR, L. ... et al, 2018. Kinetic resolution of secondary allylboronates and their application in the synthesis of homoallylic amines. Chemistry: a European journal, doi:10.1002/chem.201804395.
Abstract: 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.
Description: This paper is closed access until 12 months after the date of publication.
Sponsor: 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.
Version: Accepted for publication
DOI: 10.1002/chem.201804395
URI: https://dspace.lboro.ac.uk/2134/34820
Publisher Link: https://doi.org/10.1002/chem.201804395
ISSN: 0947-6539
Appears in Collections:Closed Access (Chemistry)

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