Enantioselective Rhodium-Catalyzed Allylation of Cyclic Imines with Potassium Allyltrifluoroborates

Hamish B. Hepburn; Nawasit Chotsaeng; Yunfei Luo; Hon Wai Lam

doi:10.1055/s-0033-1339499

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2649-2661
DOI: 10.1055/s-0033-1339499

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Enantioselective Rhodium-Catalyzed Allylation of Cyclic Imines with Potassium Allyltrifluoroborates

Hamish B. Hepburn

EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK Fax: +44(131)6506453 Email: h.lam@ed.ac.uk

,

Nawasit Chotsaeng

EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK Fax: +44(131)6506453 Email: h.lam@ed.ac.uk

,

Yunfei Luo

EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK Fax: +44(131)6506453 Email: h.lam@ed.ac.uk

,

Hon Wai Lam*

EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK Fax: +44(131)6506453 Email: h.lam@ed.ac.uk

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Abstract

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Abstract

This article presents further examples of the enantioselective rhodium-catalyzed addition of potassium allyltrifluoroborates to cyclic imines. A wide range of substituted allyl-trifluoroborates are compatible with this process, and provide protected homoallylic amines with high levels of diastereo- and enantioselection. The reactions display a strong preference for carbon–carbon bond formation at the more substituted terminus of the allyl fragment of the allyltrifluoroborate, regardless of the position of the boron atom. Representative examples of manipulation of the products are also described.

Key words

allyltrifluoroborates - asymmetric catalysis - enantioselectivity - imines - rhodium

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References

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Supporting Information