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. 2010 Aug 18;132(32):11009-11.
doi: 10.1021/ja103838d.

Cu(I)-catalyzed regioselective diamination of conjugated dienes via dual mechanistic pathways

Affiliations

Cu(I)-catalyzed regioselective diamination of conjugated dienes via dual mechanistic pathways

Baoguo Zhao et al. J Am Chem Soc. .

Abstract

This paper describes the Cu(I)-catalyzed regioselective diamination of conjugated dienes using di-tert-butyldiaziridinone as nitrogen source. The internal diamination and terminal diamination likely proceed via two mechanistic pathways. Various dienes can be efficiently diaminated at the internal double bonds with high regio- and diasteroselectivity in good yield using inexpensive CuBr as catalyst.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Proposed dual mechanisms for the Cu(I)-catalyzed diamination of conjugated dienes
Scheme 5
Scheme 5
Addition of radical B to the internal double bond

References

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