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Iridium-Catalyzed 1,3-Dipolar Cycloadditions

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Iridium Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 34))

Abstract

1,3-Dipolar cycloaddition reactions (DCR) are atom-economic processes that permit the construction of heterocycles. Their enantioselective versions allow for the creation of up to four adjacent chiral centers in a concerted fashion. In particular, well-defined half-sandwich iridium (III) catalysts have been applied to the DCR between enals or methacrylonitrile with nitrones. Excellent yield and stereoselectivities have been achieved. Support for mechanistic proposals stems from the isolation and characterization of the true catalysts.

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Notes

  1. 1.

    With the homologous rhodium complex (S Rh,R C)-[(η5-C5Me5)Rh{(R)-Prophos}(methacrylonitrile)](SbF6)2 as catalyst, up to ten consecutive catalytic runs have been performed for the reaction between methacrylonitrile and the nitrone 3,4-dihydroisoquinoline N-oxide (V). Yield decreases from 97% (first run) to 84% (tenth run) and enantioselectivity remains essentially constant at 90% ee.

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Acknowledgments

The authors thank financial support from Ministerio de Ciencia e Innovación (MICINN, Spain) and FEDER (Grant CTQ2009/10303BQU) and MULTICAT, Consolider Ingenio-2010 (CSD2009-00050).

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Authors and Affiliations

  1. Instituto de Ciencia de Materiales de Aragón, University of Zaragoza-CSIC, Pedro Cerbuna 12, 50009, Zaragoza, Spain

    Daniel Carmona & Luis A. Oro

Authors
  1. Daniel Carmona
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  2. Luis A. Oro
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Corresponding author

Correspondence to Daniel Carmona .

Editor information

Editors and Affiliations

  1. Dept. Biochemistry & Organic Chemistry, Uppsala University, Uppsala, Sweden

    Pher G. Andersson

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Carmona, D., Oro, L.A. (2011). Iridium-Catalyzed 1,3-Dipolar Cycloadditions. In: Andersson, P. (eds) Iridium Catalysis. Topics in Organometallic Chemistry, vol 34. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-15334-1_8

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