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Control of Asymmetry in the Radical Addition Approach to Chiral Amine Synthesis

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Stereoselective Formation of Amines

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 343))

Abstract

The state-of-the-science in asymmetric free radical additions to imino compounds is presented, beginning with an overview of methods involving stereocontrol by various chiral auxiliary approaches. Chiral N-acylhydrazones are discussed with respect to their use as radical acceptors for Mn-mediated intermolecular additions, from design to scope surveys to applications to biologically active targets. A variety of aldehydes and ketones serve as viable precursors for the chiral hydrazones, and a variety of alkyl iodides may be employed as radical precursors, as discussed in a critical review of the functional group compatibility of the reaction. Applications to amino acid and alkaloid synthesis are presented to illustrate the synthetic potential of these versatile stereocontrolled carbon–carbon bond construction reactions. Asymmetric catalysis is discussed, from seminal work on the stereocontrol of radical addition to imino compounds by non-covalent interactions with stoichiometric amounts of catalysts, to more recent examples demonstrating catalyst turnover.

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Acknowledgment

The generous support by NSF (CHE-0096803 and CHE-0749850) and NIH (R01-GM67187) of our radical addition chemistry method development and applications to natural product synthesis is acknowledged with gratitude. Portions of this chapter are excerpted from a previous Topics in Current Chemistry volume: Gregory K. Friestad “Asymmetric Radical Addition to Chiral Hydrazones.” In Topics in Current Chemistry: Radicals in Synthesis III. Gansauer A, Heinrich M (eds). Springer-Verlag: Berlin, 2012, vol. 320, pp. 61–92.

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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. Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York, USA

    Wei Li

  2. Department of Chemistry & Chemical Biology, Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey, USA

    Xumu Zhang

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Friestad, G.K. (2013). Control of Asymmetry in the Radical Addition Approach to Chiral Amine Synthesis. In: Li, W., Zhang, X. (eds) Stereoselective Formation of Amines. Topics in Current Chemistry, vol 343. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_481

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