Jump to main content
Jump to site search

Issue 15, 2000
Previous Article Next Article

Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: synthesis of (S)-2-arylpropanoic acids

Author affiliations

Abstract

Poly-(D)-leucine-catalysed epoxidation of chalcone furnished epoxide (+)-6; treatment of this epoxide with trimethylaluminium followed by zinc borohydride reduction and oxidative cleavage furnished (S)-2-phenylpropanoic acid 11. In a complementary sequence epoxy ketones (−)-6 and 25 were converted into (S)-2-phenylpropanoic acid and (S)-fenoprofen 5 respectively by reduction with zinc borohydride, reaction with trimethylaluminium and oxidative cleavage. Similarly epoxy ketones (−)-6, 21 and 28 were treated with methylmagnesium iodide, trimethylaluminium and the resultant alcohols subjected to oxidative cleavage to afford (S)-2-phenylpropanoic acid (from the first two substrates) and (S)-naproxen 1.

Back to tab navigation

Article information


Submitted
07 Feb 2000
Accepted
17 Mar 2000
First published
02 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2455-2463
Article type
Paper

Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: synthesis of (S)-2-arylpropanoic acids

L. Carde, D. H. Davies and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 2000, 2455
DOI: 10.1039/B000996M

Search articles by author

Spotlight

Advertisements