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Synthesis 2004(3): 401-404
DOI: 10.1055/s-2004-815929
DOI: 10.1055/s-2004-815929
PAPER
© Georg Thieme Verlag Stuttgart · New YorkIsoxazoles as Latent Siloxybutadienes: An Easy Entry to Polyfunctionalized Benzene Systems via Diels-Alder Reaction with Acetylenes
Further Information
Received
22 November 2003
Publication Date:
26 January 2004 (online)
Publication History
Publication Date:
26 January 2004 (online)
Abstract
Base-induced or reductive cleavage of isoxazole rings followed by silylation of the resulting open-chain products affords bis(siloxy)butadienes in high yields. Their synthetic usefulness in the construction of multifunctionalized aromatic systems, via Diels-Alder reactions, is shown. The ability of bis(siloxy)butadienes to undergo deprotonation and reaction with electrophiles is also studied.
Key words
isoxazoles - siloxybutadienes - silyl dienol ethers - Diels-Alder cycloaddition - β-diketones
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