Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 28, Pages 4751-4754Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800710
Keywords
density functional calculations; isocyanides; reaction mechanisms; E/Z isomerism; glycosylation
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Funding
- Wenner-Gren Foundation
- Swedish Research Council (VR)
- Carl Trygger Foundation
- Magn Bergvall Foundation
- Swedish National Infrastructure for Computing, SNIC [023/07-18]
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We present a computational investigation of the reaction between isocyanides and carboxylic acids. Our results indicate that this reaction begins with a stereoselective concerted alpha-addition of the acid to the isocyanide, leading exclusively to a Z-acyl imidate. Isomerization to the E isomer and successive rate-limiting 1,3 O -> N acyl migration yields an N-formyl imide. The calculated barriers are in good agreement with the experimental reaction conditions. Our results might provide an explanation for the peculiar reactivity observed when this reaction is carried out in a self-assembled capsule. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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