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

Viveca Thornqvist, Sophie Manner, Torbjörn Frejd

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12 Citations (SciVal)

Abstract

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.
Original languageEnglish
Pages (from-to)410-415
JournalTetrahedron: Asymmetry
Volume17
Issue number3
DOIs
Publication statusPublished - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

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