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Cram's rule for radicals: Stereoselective hydrogen abstraction reactions of NH substituted radicals by Dennis P. Curran; Shunneng Sun is a Chemistry article available to read on EtoBox.

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## Radical reductions of chid thiazolidines with (TMS)3SiH reveal stereochemical parallels between ionic reactions afketonednines and radical reaclions ofaminoa&l radicals bear@ IWR substituents. Related classes of ionic and radical reactions often show sustained stereochemicsl parallels.1 In substrate controlled 1.2-asymmetric induction, parallels are observed between carbonyl-substituted radicals and enolatesz and between oxygen-substituted radicals and ketones/aldehydes3 Stereoselective reactions of carbonyl-substituted radicals and enolates both follow A-strain models, while reactions of oxygen-substituted radicals and ketones both follow Felkin-Anh models. These two models (which usually predict opposite products) are often pitted against each other in the case of nitrogen substituted radicals (Figure 1). We4a and Renaud 4b have recently shown that reactions of nitrogen-substituted radicals with large RE and Rz groups follow the A-strain model. This makes sense because transition states with "Felkin-Anh" conformations will be destabilized by interactions between Rz and the medium or large sized group.5

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Author

Dennis P. Curran; Shunneng Sun

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1993

Language

EN

Field

Chemistry (Physical Sciences)