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Radical Additions to Chiral Hydrazones: Stereoselectivity and Functional Group Compatibility

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Radicals in Synthesis III

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 320))

Abstract

Free radical additions to imino compounds offer increased synthetic accessibility of chiral amines, but lack of general methods for stereocontrol has hindered their development. This review focuses on two asymmetric amine synthesis strategies designed to address this problem, with emphasis on addition of functionalized radicals which may facilitate applications to synthesis of complex targets. First, chiral N-acylhydrazones are acceptors for intermolecular radical additions of a wide range of primary, secondary, and tertiary alkyl halides to the C=N bond, with radicals generated under manganese-, tin-, or boron-mediated conditions. A variety of aldehydes and ketones serve as viable precursors for the chiral hydrazones, and the highly stereoselective reactions tolerate electrophilic functionality in both coupling components. Second, radical precursors may be linked to chiral α-hydroxyhydrazones via a silicon tether to the hydroxyl group; conformational constraints impart stereocontrol during 5-exo radical cyclization under stannyl- or thiyl-mediated conditions. The silicon tether may later be removed to reveal the formal adducts of hydroxymethyl, vinyl, acetyl, and 2-oxoethyl radicals to the C=N bond. Methodology development and applications to biologically important targets are discussed.

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Notes

  1. 1.

    An alternative 2-step procedure involving prior removal of the acetonide [(1) 0.1 M methanolic HCl; (2) HgCl2 aq CH3CN] afforded the same mixture in 23% yield.

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Acknowledgment

Generous support for our programs in radical addition methods and applications to natural products by NSF (CHE-0096803 and CHE-0749850) and NIH (R01-GM67187) are deeply appreciated. Research Corporation, Petroleum Research Fund, and Vermont EPSCoR have also provided funding for parts of this work. Many devoted students and postdoctoral associates are responsible for developing our program in chiral amine synthesis, and their efforts are gratefully acknowledged. This chapter was prepared during an appointment as an Obermann Scholar in the Obermann Center for Advanced Studies (University of Iowa) which is acknowledged with appreciation.

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  1. Department of Chemistry, University of Iowa, Iowa City, IA, 52242, USA

    Gregory K. Friestad

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  1. Gregory K. Friestad
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Correspondence to Gregory K. Friestad .

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  1. LS für Organische Chemie I, TU München, Lichtenbergstr. 4, Garching, 85747, Germany

    Markus Heinrich

  2. Kekulé-Institut für Organische, Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, Bonn, 53121, Germany

    Andreas Gansäuer

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Friestad, G.K. (2011). Radical Additions to Chiral Hydrazones: Stereoselectivity and Functional Group Compatibility. In: Heinrich, M., Gansäuer, A. (eds) Radicals in Synthesis III. Topics in Current Chemistry, vol 320. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_163

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