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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
See this image and copyright information in PMC

References

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    1. For dirhodium-catalyzed oxidation see: Catino AJ, Forslund RE, Doyle MP. J. Am. Chem. Soc. 2004;126:13622. Catino AJ, Nichols JM, Choi H, Gottipamula S, Doyle MP. Org. Lett. 2005;7:5167.

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