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Issue 39, 2015
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An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement

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Abstract

A new method for the asymmetric synthesis of β-aryl alanines is reported. The developed strategy is based on Pd(0)-catalyzed cross-coupling of chiral allyl alcohols with arylboronic acids followed by Ichikawa sigmatropic rearrangement of allyl cyanates to isocyanates. In the rearrangement step the allyl alcohol is stereospecifically transformed into the corresponding allylamine with complete chirality transfer. The resulting allylamines are converted into β-aryl alanines after oxidation of the double bond.

Graphical abstract: An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement

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Publication details

The article was received on 13 Feb 2015, accepted on 20 Mar 2015 and first published on 20 Mar 2015


Article type: Paper
DOI: 10.1039/C5RA02818C
Citation: RSC Adv., 2015,5, 30882-30888
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    An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement

    P. Szcześniak and S. Stecko, RSC Adv., 2015, 5, 30882
    DOI: 10.1039/C5RA02818C

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