Diastereoselection during allylindium addition to norbornyl α-diketones

Khan, Faiz Ahmed ; Dash, Jyotirmayee (2004) Diastereoselection during allylindium addition to norbornyl α-diketones European Journal of Organic Chemistry, 2004 (12). pp. 2692-2700. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.200400044


We 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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Allylation; Diastereoselectivity; α-Diketones; Indium; Regioselectivity
ID Code:79669
Deposited On:27 Jan 2012 14:51
Last Modified:27 Jan 2012 14:51

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