Abstract
AbstractWe report a highly regio‐ and diastereoselective allylindium addition to norbornyl α‐diketones that leads to acyloins. The diastereoselection in the case of monosubstituted derivatives greatly depends on the nature of the 5‐endo substituents. Non‐chelating groups direct the addition from the sterically less congested exo‐face, diagonal to the substituent, while chelating substituents, such as an alkoxy or acetoxy units, induce a complete reversal in the selectivities. The presence of an oxygen atom directly linked to the norbornyl framework is crucial for eliciting a chelating effect because an acetoxymethyl (−CH2OAc) group exhibits normal behavior and acts as a non‐chelating group. The dramatic influence (reversal) of an apparently innocuous exo‐Me substituent is noted. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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