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Wagner A, Hampel N, Zipse H, et al. Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Org Lett. 2015;17(19):4770-3doi: 10.1021/acs.orglett.5b02319.
Wagner, A., Hampel, N., Zipse, H., & Ofial, A. R. (2015). Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Organic letters, 17(19), 4770-3. https://doi.org/10.1021/acs.orglett.5b02319
Wagner, Alexander, et al. "Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines." Organic letters vol. 17,19 (2015): 4770-3. doi: https://doi.org/10.1021/acs.orglett.5b02319
Wagner A, Hampel N, Zipse H, Ofial AR. Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Org Lett. 2015 Oct 02;17(19):4770-3. doi: 10.1021/acs.orglett.5b02319. PMID: 26372780.
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Org Lett. 2015 Oct 02;17(19):4770-3. doi: 10.1021/acs.orglett.5b02319.

Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines.

Organic letters

Alexander Wagner, Nathalie Hampel, Hendrik Zipse, Armin R Ofial

Affiliations

  1. Department Chemie, Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, 81377 München, Germany.

PMID: 26372780 DOI: 10.1021/acs.orglett.5b02319

Abstract

Iron-catalyzed oxidative α-cyanations at tertiary allylamines in the allylic position are followed by anti-Markovnikov additions of alcohols across the vinylic CC double bonds of the initially generated α-amino nitriles. These consecutive reactions generate 2-amino-4-alkoxybutanenitriles from three reactants (allylamines, trimethylsilyl cyanide, and alcohols) in one reaction vessel at ambient temperature.

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