Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation

Summary, in English

A recent new strategy for the transformation of mono-dioxolane protected 1,3-cyclohexadione into bridgehead hydroxyl bicyclo[2.2.2]octane derivatives, based on allylindation followed by ozonolysis and intramolecular aldol addition, was modified to include asymmetric allylindation. This enabled the first enantioselective synthesis of (1R,4R,6S)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one and (1S,4S,6R)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one in high enantiomeric excess. Issues concerning the non-reproducibility of the asymmetric allylindation were also addressed. (c) 2006 Elsevier Ltd. All rights reserved.

• Author: Viveca Thornqvist; Sophie Manner; Torbjörn Frejd
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2006
• Language: English
• Pages: 410-415
• Publication/Series: Tetrahedron: Asymmetry
• Volume: 17
• Issue: 3
• Links: http://dx.doi.org/10.1016/j.tetasy.2005.12.026
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 0957-4166