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Converting chair-like transition states into zig-zag projections

A method of drawing stereochemical structures

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Abstract

A short and easy method for the conversion of chair-like transition states into zig-zag projections using planar cyclohexane structures, and also the concepts of change of bond in the plane and group swap by rotation are described. Some common reactions where this method could be used to draw products include: aldol reaction, [3,3] sigmatropic rearrangements, allylation and crotylation of aldehydes, and formation of lithium enolates.

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Suggested Reading

  1. J Clayden, N Greeves, S Warren and P Wothers, Organic Chemistry, Oxford University Press, Oxford, p.900, 2007.

    Google Scholar 

  2. G Procter, Stereoselectivity in Organic Synthesis, Oxford Chemistry Primer no. 63, Oxford University Press, Oxford, pp.43–51, 1998.

    Google Scholar 

  3. A Mehta, Directed Aldol Synthesis: Part 2 — Syn and Anti control using Zimmerman Traxler principle. http://pharmaxchange.info/press/2011/08/directed-aldol-synthesis-part-2-syn-and-anti-control-using-zimmerman-traxler-principle/ (accessed June 2013).

  4. P Wyatt, S Warren, Organic Synthesis: Strategy and Control, Wiley, Chichester, pp.380–381, 2007.

    Google Scholar 

  5. J M Hornback, Organic Chemistry, 2nd Ed., Thomson Brooks/Cole, U.S., pp. 205–214, 2006.

    Google Scholar 

  6. D Klein, Organic Chemistry, John Wiley & Sons, Inc., U.S., pp.167–174, 2012.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, The University of Tulsa 800, South Tucker Driver, Tulsa, OK, 74104, USA

    Syed R. Hussaini

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  1. Syed R. Hussaini
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Correspondence to Syed R. Hussaini.

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Hussaini, S.R. Converting chair-like transition states into zig-zag projections. Reson 19, 846–850 (2014). https://doi.org/10.1007/s12045-014-0094-y

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  • DOI: https://doi.org/10.1007/s12045-014-0094-y

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