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By William Lee Jolly

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Extra resources for Inorganic Syntheses: v. 11

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Erkkilä, Department of Chemistry, Helsinki University of Technology, P. O. B. 6100, FI-02015 TKK, Espoo, Finland 30 31 31 33 41 41 50 54 57 62 62 65 67 68 30 P. M. Pihko et al. 1 Introduction As nucleophiles, simple alkenes are typically so unreactive that only highly active electrophiles, such as carbocations, peroxides, and halogens will react with them. For the generation of carbon-carbon bonds, milder methods will often be required. Fortunately, it is possible to increase the reactivity of alkene-type p-nucleophiles by introducing electron-donating substituents.

Instead of using TADDOL, they selected one methanol molecule, two methanol molecules and 1,4-butanediol in cooperative and bifurcated coordination as catalysts. It was found that cooperative catalysis is generally the favored route. Ding, Wu et al. [58] used a model system consisting of benzaldehyde and a modified Danishefsky’s diene, in which the trimethylsilyl group was replaced by a methyl group. They varied the aryl substituents of the TADDOL catalyst, and the results for the most enantioselective 1-naphthyl substituted catalyst were presented in detail.

The assignment used in here is based on the original formalism by Diels and Alder 3 Noncovalent Organocatalysis Based on Hydrogen Bonding 25 reaction exhibited a clear energetic preference for the endo- over the exo-approach. Thus, only endo transition states were considered. The number of possible reaction paths/transition states is thus reduced from eight to two, namely endo-approach with re- or si-face attack of the model diene to the activated benzaldehyde. 2 kcal mol−1). The reaction proceeds via a concerted but asynchronous pathway, and no zwitterionic intermediate or transition state corresponding to a stepwise Mukaiyama-aldol type pathway could be located.

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