Asymmetric Methods for Radical Addition to Imino Compounds

Free radicals, which in the past were considered unruly chemical species, have become manageable and indispensable for synthetic organic chemistry. The unique nature of free radicals has allowed practitioners in organic synthesis to design flexible approaches to produce various materials ranging from small molecules to polymers. The present Personal Account describes the author's endeavors to create molecular complexity by the strategic use of free radicals, with an emphasis on the synthesis of bioactive natural products.

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

Friestad

2013

Stereoselective Formation of Amines

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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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Asymmetric Methods for Radical Addition to Imino Compounds

Cited by 3 publications

References 129 publications

ChemInform Abstract: Asymmetric Methods for Radical Addition to Imino Compounds

ChemInform Abstract: Asymmetric Methods for Radical Addition to Imino Compounds

Endeavors to Access Molecular Complexity: Strategic Use of Free Radicals in Natural Product Synthesis

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

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