PAPER	Synthesis 2006: 3621-3624   DOI: 10.1055/s-2006-950294
© 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
Received 31 July 2006

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.

Key words

enones - heterocycles - lactones - spiro compounds