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Synfacts 2011(5): 0493-0493  
DOI: 10.1055/s-0030-1259795
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

A Well-Oiled Stereodynamic Probe

Contributor(s): Timothy M. Swager, Olesya Haze
D. P. Iwaniuk, C. Wolf*
Georgetown University, Washington, USA
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

A series of Sonogashira cross-­coupling reactions is employed in the synthesis of the aryl-acetylene stereodynamic probe 1, which was obtained in 62% overall yield. While 1 is achiral, condensation with chiral di- or monoamines produces axially chiral diimines (e.g. 2). Because of the unhindered rotation in 1 (blue arrows) the central-to-axial chirality induction is essentially ‘frictionless’.