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. 2006 May 3;128(17):5648-9.
doi: 10.1021/ja061146m.

The oxidative mannich reaction catalyzed by dirhodium caprolactamate

Arthur J Catino  1 , Jason M Nichols, Brian J Nettles, Michael P Doyle
Affiliations

The oxidative mannich reaction catalyzed by dirhodium caprolactamate

Arthur J Catino et al. J Am Chem Soc. .

Abstract

Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable gamma-aminoalkyl butenolides are obtained.

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Figures

Figure 1
Figure 1
Iminium ion formation and nucleophilic capture
Scheme 1
Scheme 1
Scheme 2
Scheme 2
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References

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