Invited Academic Review - Organic Process ... - ACS Publications

It is our pleasure to introduce an invited contribution from Professor Peter Wipf of the University of Pittsburgh featuring work from his laboratories...
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Invited Academic Review

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t is our pleasure to introduce an invited contribution from Professor Peter Wipf of the University of Pittsburgh featuring work from his laboratories on Allylic Amines as Key Building Blocks in the Synthesis of (E)-alkene Peptide Isosteres. This account highlights the nucleophilic-imine addition with vinyl organometallics to provide an efficient, practical, and highyielding entry for generation of structurally diverse and highly versatile allylic amines. This novel methodology has been successfully applied to the synthesis of mitochondrial targeting agents JP4-039 and XJB-131 and other analogues in reasonable quantities. This methodology clearly highlights that peptide-containing analogues can be constructed into gram quantities due to the robust synthetic access via Professor Wipf’s newly developed hydro(carbo)metalation−transmetalation−imine addition protocol. We believe this chemistry has a high value for process chemists seeking practical synthetic methods for industrial applications.

Chris Senanayake Stéphane Caron, Members of the Editorial Advisory Board, Organic Process Research & Development

Published: January 4, 2012 © 2012 American Chemical Society

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dx.doi.org/10.1021/op2003166 | Org. ProcessRes. Dev. 2012, 16, 25−25