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Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes

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posted on 2019-09-18, 14:37 authored by Kay Yeung, Rebecca E. Ruscoe, James Rae, Alexander P. Pulis, David J. Procter
A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units.

Funding

We thank the University of Manchester (President's Scholarship to K.Y. and Lectureship to A.P.P.), the SCI (Scholarship to K.Y.), the BBSRC (DTP Studentship to R.E.R.), and the EPSRC (Studentships to K.Y. and J.R. and Established Career Fellowship to D.J.P.).

History

Citation

Angewandte Chemie International Edition, 2016, 55 (39), pp. 11912-11916

Author affiliation

/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry

Version

  • VoR (Version of Record)

Published in

Angewandte Chemie International Edition

Publisher

Wiley for Gesellschaft Deutscher Chemiker (GDCh)

issn

1433-7851

Copyright date

2016

Available date

2019-09-18

Publisher version

https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201606710

Notes

Supporting information for this article can be found under: http://dx.doi.org/10.1002/anie.201606710

Language

en

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