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://doi.org/10.1002/ejoc.200400044

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

Abstract

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.
ID Code:126468
Deposited On:17 Oct 2022 05:54
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