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Synthesis 2010(13): 2297-2307  
DOI: 10.1055/s-0029-1218800
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Gold Catalysis: Desymmetrization in the Furan-Yne Reaction

A. Stephen K. Hashmi*a, Michael Wölfleb, Filiz Ataa, Wolfgang Freyb, Frank Romingera
a Organisch-Chemisches Institut, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Fax: +49(6221)544205; e-Mail: hashmi@hashmi.de;
b Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
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Publication History

Received 5 May 2010
Publication Date:
27 May 2010 (online)

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Abstract

A series of seven symmetric difuryl-diynes were synthesized by a route delivering an anti-configurated product as the major product. The gold-catalyzed conversion of the individual anti- and syn-diastereomers was investigated. The anti-diastereomer in a desymmetrization reaction chemoselectively delivered dihydro­indenediols with a furyl and a 2-oxopropyl side chain. The syn-dia­stereomer was completely converted into oligomeric/polymeric material. Thus, it was not necessary to separate the minor amount of the syn-diastereomers from the product mixtures in order to isolate the dihydroindenediols.

Key words

alkynes - alcohols - furans - gold - homogeneous catalysis - ketones

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