Leading Question
Are there other examples of this reaction?
Our reaction details the one step preperation of tert-butyl but-3-ynyl(tosyl)carbamate, or Molecule 301 (see Figure 1) from 3-butyn-1-ol. This preperation of a sulfonamide group (see Figure 2) can also be accomplished by an intramolecular reaction. Two examples, taken from current articles in well-known chemistry journals, depict this reaction.
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The first example comes from:
                        Bohnstedt, A.C.; Bruendl, M.M.; Feldman, K.S.; Schildknegt, K. J. Org.
                        Chem. 1996, 61, 5440-5442.
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The second example comes from: Dauban, P.; Dodd, R.H. Org. Lett. 2000, 2, 2327-2329.
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1Becker, M.H.; Chua, P.; Downham, R.; Douglas, C.J.; Garg, N.K.; Hiebert, S.; Jaroch, S.; Matsuoka, R.T.; Middleton, J.A.; Ng, F.W.; Overman, L.E. J. Am. Chem. Soc. 2007, 129, 11987-12002.

Designed by Nikola Collins, James DeRosier and Justin Zehtabzadeh - April 2008