Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate

Kousuke Tani and Brian M. Stoltz ()
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Kousuke Tani: California Institute of Technology
Brian M. Stoltz: California Institute of Technology

Nature, 2006, vol. 441, issue 7094, 731-734

Abstract: Amides with a twist The amide bond is ubiquitous in chemistry and biology. In acyclic compounds, amide bonds are often planar. In bicyclic bridgehead lactams, however, amide groups are highly twisted, and a 1938 publication by Czech chemist Rudolf Lukeš drew attention to the intriguing properties of these ‘twisted amides’. Intriguing yes, but hard to make. Now Kousuke Tani and Brian Stoltz report the first unambiguous synthesis, isolation, and X-ray crystallographic characterization of a compound containing a twisted amide bond. The synthesis avoids the conventional route for classical amide bond formation, and the availability of compounds made in this way should lead to a greater understanding of the properties of amide bonds.

Date: 2006
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DOI: 10.1038/nature04842

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