Synthesis 2006(21): 3621-3624  
DOI: 10.1055/s-2006-950294
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Approach to the Synthesis of Allylic Spiro Ethers and Lactones

Ming-Chang P. Yeh*, Yi-Chin Lee, Tsao-Ching Young
Department of Chemistry, National Taiwan Normal University, Taipei 117, Taiwan
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Publikationsverlauf

Received 31 July 2006
Publikationsdatum:
09. Oktober 2006 (online)

Abstract

Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)-substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.