Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines

Laura Villar; Nikolai V Orlov; Nikolay S Kondratyev; Uxue Uria; Jose L Vicario; Andrei V Malkov

doi:10.1002/chem.201804395

Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines

Chemistry. 2018 Nov 2;24(61):16262-16265. doi: 10.1002/chem.201804395. Epub 2018 Oct 9.

Authors

Laura Villar¹, Nikolai V Orlov², Nikolay S Kondratyev², Uxue Uria¹, Jose L Vicario¹, Andrei V Malkov²

Affiliations

¹ Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080, Bilbao, Spain.
² Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK.

PMID: 30175420
DOI: 10.1002/chem.201804395

Abstract

Highly enantioenriched, chromatographically-stable secondary allyl boronates featuring a 1,1,2,2-tetraethyl-1,2-ethanediol fragment (Epin) were obtained by kinetic resolution of their racemic mixtures. The Epin group at boron considerably improved stability of allyl boronates allowing them to be readily isolated by chromatography on silica. 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.

Keywords: allylation; amines; asymmetric synthesis; kinetic resolution; stereoselectivity.

Abstract

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